Oren Klaff
@orenklaff
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Bestselling author of Pitch Anything & Flip the Script. Investment banker, entrepreneur, master of persuasion. Teaching you to win deals & influence people.
Carlsbad, CA
Joined January 2011
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
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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,
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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
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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
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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
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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
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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
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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.
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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.
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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
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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
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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
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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 -
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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.
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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
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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
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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
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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
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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
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