The Spiro Circle

Datarails CRO Aviv Canaani has an unusual vantage point. He runs the full revenue engine of the financial planning and analysis platform for Microsoft Excel users — sales, marketing, partnerships — from New Jersey, while his marketing team operates out of Israel. He relocated to be closer to the North American customer base as the marketers stayed put. And after years of sitting inside both ecosystems at the same time, attending CMO sessions in Tel Aviv and building pipelines in the US, he’s reached a verdict most people in his position wouldn’t say out loud: the Israelis are better.It’s a claim that cuts against the instinct of almost every Israeli founder he’s encountered - and every company I’ve spoken to over the years. “Normally, when I speak to startups that are born in Israel, they want to send their sales and marketing overseas immediately. [It’s] the first thing they want to do,” I told him during our conversation. But Canaani’s experience runs the other direction.The Israeli edge, he claims, comes down to a cultural obsession with output. “When you talk with people in Israel, marketing leaders, it’s about how they built machines, how much the cost per meeting, how they’re running campaigns on Facebook and Google and all that.” American counterparts, he finds, often arrive at the conversation from somewhere else entirely. “A lot of CMOs and people in marketing I talk with in the US or Canada… can talk more about the brand, how things take time, like it’s a long-term investment.”“Tachas mentality” explained He traces this back to something structural in Israel’s tech DNA: The concentration of adtech companies and the performance-marketing culture they seeded, and also what he calls “tachas mentality”. He explained that this requires teams to be focused on results above everything else. The blend of that mindset with an unusually international talent pool (many ‘Olim’ from Britain, the US, or Europe) produces something Canaani finds hard to replicate in America.But there’s a catch - and one worth remembering. The same intensity that makes Israeli marketing so effective in the early stages carries a structural weakness as companies grow. “In North America, things are much more organized. It’s clearer how they create the messaging and the product marketing and how to make sure there is alignment between marketing and sales,” he told me. Israel, by contrast, tends to run so fast that alignment becomes a casualty. “It seems like sometimes it doesn’t even matter if marketing speaks one language and sales speaks another. Let’s just run fast. It’s speed above everything else.” The American advantage, then, is less about raw marketing talent and more about institutional discipline. “In North America, maybe it’s hard in the startup phase, but once they’re a bigger company, they have better processes — how to run things, how to stay on point.”So what Canaani is describing is a stage-mapping problem. Israeli performance marketing is almost perfectly calibrated for the zero-to-one phase: find the signal, iterate fast, fill the pipeline before the runway ends. But American marketing discipline becomes the dominant advantage once you’re scaling and when the team is distributed. Move fast and break things, but then slowly mold them into greatness.The companies that figure out how to sequence both are the ones most likely to build something that lasts. Datarails, with teams operating on both sides and a CRO who has lived inside both cultures simultaneously, is running that experiment right now. [5-minute preview: Why Israeli Startups Are Better at Marketing Than They Think] Get full access to The Spiro Circle at www.thespirocircle.com/subscribe

Every few years, a new American administration arrives in the Middle East convinced it can start fresh. Trump’s team was no different. They came to the problem with a clean slate and nothing but the confidence of a New York real estate mogul. They produced two documents across both his terms: the January 2020 plan and the October 2025 twenty-point Gaza framework.The result, according to my guest Gidi Grinstein, was that they landed exactly where everyone always lands.“Even Trump ends up landing very close to where Nixon landed, to where Carter landed, to where Clinton landed,” he told me. “Because there is a gravitational force that is shaping these negotiations.”Gidi Grinstein has seen the Middle East from angles most people never will. At 29, he was the secretary of Israel's negotiating delegation at Camp David and the youngest person at the 2000 Summit. He spent years inside the machinery of the peace process drafting texts, aligning teams, and managing the distance between what leaders said in public and what they were willing to accept in private. Today, he runs Tikkun Olam Makers (TOM), a global initiative using open-source 3D printing to bring affordable prosthetics to people who can't access or afford conventional ones. While we intended to speak mostly about TOM, our conversation stayed on peacebuilding, negotiation, and his view of politics today.The force, he said, traces back to “the most brilliant and American diplomat of the last hundred years”, Henry Kissinger, and the architecture he designed in the 1970s. It was a framework built not around Israeli or Palestinian interests, but around American hegemony in the Middle East. Half a century later, and it is proving so durable for Washington that no administration, however disruptive, can break from it. The 2020 Trump plan's "two nation states for two people" echoes UN Resolution 181 from 1947. The 2025 Gaza framework in places reads like a revamped version of the Oslo Declaration of Principles from 1993. “You would be stunned by the amount of similarities,” he told me.What’s interesting this time around is that both countries - Israel and the US - face impending elections mere days apart, promising to shake up not just the political makeup for both sides, but potentially the leadership of one. This creates what Grinstein calls the clock problem: Israeli and American leaders, under electoral pressure, always want a deal now. Their counterparts (Arafat then, the Iranians today) operate on an entirely different political timeline, with every incentive to wait out a weakened or transitional government.“The synchronization of the political clocks is very important in getting the deal,” he said. Trump, he suggests, may be walking into the same trap by pushing hard before November while Tehran calculates what comes after.The gravity doesn’t guarantee peace, but I realized it means the frameworks are always roughly the same so long as the Americans are involved. And so far, history is showing us that they always find their way back to them.You can catch the entire conversation above. And expect more analysis from our conversation in future newsletters. [5-minute preview: Watch Gidi explain this in a YouTube clip, “Trump Thinks He's Rewriting Middle Eastern History. He's Repeating It.”]The Spiro Circle is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber. Get full access to The Spiro Circle at www.thespirocircle.com/subscribe

As conflict dynamics shift across the Middle East, from disrupted shipping lanes to drone warfare, a new question is emerging: who controls the software behind autonomous systems?Military power used to depend on access to advanced weapons systems, often built through international supply chains and dominated by a handful of large contractors. Today, conflicts in Ukraine and Iran, and tensions with China, are highlighting bottlenecks on critical technologies and the instability of disrupted supply chains. One Israeli company may have an answer to this new challenge. Udi Oster is the co-founder of eyesAtop, a startup building AI-native universal controllers for drone fleets. The company has spent the last three years making a case that the strategic asset in modern warfare isn’t any particular drone, but it should be the operating system above them.“Locking in to one vendor with one platform is something that in today’s world is very difficult,” Oster told me. “You want to have the flexibility to get the best technology at the point of time of interest and use it immediately.”Militaries around the world are accumulating drones from dozens of manufacturers, but without a common interface, any shared AI layer, or no easy way to retrain operators when hardware changes. EyesAtop’s platform intends to integrate into any drone, from any vendor, under one controller trained on over 500,000 hours of live IDF operational data.The Spiro Circle is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.The geopolitical context of conflicts and wars has expanded this market. Global defensetech VC hit a record $49.1 billion in 2025, nearly double the prior year, driven largely by autonomy and AI. American firms like Anduril have already moved into Taiwan, South Korea, Japan, and Singapore, selling hardware to nations trying to face off against the Chinese military. eyesAtop is pursuing a different layer of the stack: not competing on the drone itself, but selling the so-called brain that integrates whatever drones those nations already operate or plan to buy.Oster draws a sharp distinction between the American market and everyone else. America is its own category: It accounts for more than half of global defense spending, it has its own procurement logic, and its own concept of operations. EyesAtop already has a U.S. co-founder, a U.S. base, and existing deals with American military commands. For the rest of the world, the company offers a full-kit solution, where it selects the best available platforms globally, integrates them under its universal controller, and delivers a turnkey reconnaissance or strike capability to militaries that lack the R&D infrastructure to build it themselves.“Most of the countries outside of the U.S. lack the infrastructure and the R&D budgets even to get to the same type of level as Israel and the U.S.,” Oster said. “I would look at these countries differently.”The fundraising backstory underscores how fast the landscape has shifted. Three years ago, Oster says, virtually no Israeli VC would touch defense. The stigma was visible and impacted reputational and commercial opportunities. But the world changed after October 7, 2023, and today, funds are competing for allocations in a sector that now ranks among the top three investment themes globally.The longer-term vision Oster sketches is more ambitious than any single product cycle. As robotic systems multiply on the battlefield, army headcount becomes less relevant than software sophistication. Today, wars can be fought by one operator controlling multiple autonomous platforms that were trained in actual combat. “Instead of having a whole company,” he says, “you have two people, but they would operate a company of robotic systems.”He calls it "the ghost squad." For the allies now looking to build drone sovereignty in the middle of an active regional war, it may also be the next software contract they don't know they need. And that balance of power is moving up the stack.[3-minute preview: Optimism in Defensetech and the future of deterrence] Get full access to The Spiro Circle at www.thespirocircle.com/subscribe