8 takeaways from the latest episode with
Amiram Shachar, CEO of
Upwind Security
Before Upwind, Amiram built Spot out of a university final project his professors tried to talk him out of. He sold it for $450M. Today he runs Upwind: 3.5 years old, 500+ employees, 400+ enterprise customers, $450M raised - competing against some of the best companies cybersecurity has ever produced.
1. Not a single VC wanted to invest in Spot.
The answer he kept getting from VCs: "Show me another company that succeeded at reducing cloud costs." There wasn't one. Customers did want the product - the VCs just hadn't caught up yet. He listened to the customers and built it anyway.
2. When Amazon gives your product away for free, that's not the end of the game. It's the signal that the market is real.
Amiram found an old Jeff Bezos interview that kept him sane. People on the outside look at competition like an NBA final - one winner, one loser. In big markets it's the opposite. When more companies come in, customers understand the category matters. They're doing your marketing for you. Especially in a new market.
3. He didn't come from the industry - and that was exactly the advantage.
"We're not security people from Unit 8200, we're DevOps people." That's why they saw what others didn't: you can't protect a cloud that's constantly changing by taking a snapshot from the outside once a day. The real-time approach came out of that.
4. Strategy is not a retreat in the desert.
"Real strategy isn't going off to the desert to think about what happens in 2030." It's sitting with customers on the roadmap from 11pm to 1am, showing them where you're going, absorbing the feedback, and moving from there.
5. An eye roll is data too.
Sometimes the hard feedback isn't the hard questions - it's the customer rolling their eyes. And not just feedback: inaction counts too. "If someone doesn't walk out of a conversation saying 'this is amazing,' you need to understand why that didn't happen, and fix it accordingly."
6. Validation never ends.
We talk about validation like it's an early stage. In practice, the moment you ship a new product, you're right back there. Amiram does it regularly as the CEO of a company with 400 customers.
7. The four jobs of a CEO, according to Amiram:
Never run out of money. Never run out of vision and roadmap. Take care of talent - bring in the best people, and make sure only the best stay. And inspire: open up the prism for everyone so they see how big the thing they're building actually is.
8. Pressure isn't anxiety. It depends what you do with it.
"Most of the anxiety in our lives comes from not taking action." Even if the problem isn't solved — if you walked out of the room with one action to take, you already feel different. Amiram turns pressure into adrenaline and proactivity, not paralysis.
Full episode in the comments (in Hebrew)👇
In the photo: Amiram with one of his investors
Idan Tamir,
GUTS - Harel Innovation hub
Itamar Mainemer