The Spiro Circle

James Spiro
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Join me as I discuss issues relating to Israel, tech, media, and news. Sometimes with a guest, sometimes solo. www.thespirocircle.com

  1. AI Didn’t Break the Cloud. It Revealed What Was Already Broken - #0047, Roi Ravhon

    2 DAYS AGO

    AI Didn’t Break the Cloud. It Revealed What Was Already Broken - #0047, Roi Ravhon

    For years, cloud computing quietly rewired how companies build products, scale infrastructure, and manage costs. And the widespread sudden adoption of AI has accelerated it. In doing so, it exposed a far more dangerous problem than rising bills: how little most enterprises actually understand about what they’re spending and why. This week, I spoke to a company that understands how the financial stakes have changed. “We’re spending all that money on something that we’re not really sure what the ROI is,” Roi Ravhon, Co-founder and CEO of cloud cost management platform Finout, told me. What once lived in innovation budgets is now embedded directly in business fundamentals. “Now it’s part of our gross margin… It’s part of what we’re building as a service.” Founded in 2021, Finout helps enterprises monitor, allocate, and forecast cloud spending across providers, including AWS, Google Cloud, Azure, Datadog, Kubernetes, and Snowflake. The company has raised $85 million to date and works with customers such as Lyft, The New York Times, SiriusXM, Wiz, and Tenable. Not only is one problem that is AI inherently expensive, but businesses are also adopting it and transforming their practices without clarity. “AI is a lot more expensive than what we thought it would be,” Ravhon explained. “We’re not really sure how predictable it’s going to be. We’re not really sure if we’re using it effectively or not. Just buying and buying and buying more AI services.” Cloud costs were already complex before AI arrived. But today, AI workloads are priced by tokens, usage, and models that can quickly change, making it even harder to ignore. The result is cost waste that hides in plain sight. “There are so many dumb ways, it’s amazing,” Ravhon says when asked how those may materialize. The dynamic is familiar, even if the scale is not. Just as individuals may lose track of unused subscriptions, businesses can accumulate cloud services that persist simply because no one is sure what would happen if they disappeared. In some cases, the scale is staggering. Ravhon recalls working with enterprises that had “tens of millions of dollars of ‘shadow IT’”, meaning services running in the cloud that no one fully understood and no one wanted to turn off. Teams hesitate to shut anything down because it might break something, or might do nothing at all. I asked if there was a tension between the engineering teams, who are incentivized to move fast and build reliably, and the finance teams, who are accountable for budgets and forecasts. Turns out there is - and in practice, engineering usually wins. “I'm an engineer, we tend to be very defensive,” Ravhon says. “Finance sets a budget, engineering depletes it.” He adds, “It’s very easy to pick the most expensive model to sleep better at night.” Ravhon, who first spotted these kinds of gaps when he was Director of Core Engineering at Logz.io, a cloud observability company, argues the conversation needs to shift away from simply cost-cutting and toward control. “Cloud is not spend, it’s an investment,” he says. “The best way to overcome this is with data.” When asked during our quickfire round what leaders should remember from the AI cost reckoning now underway, Ravhon doesn’t hesitate. His answer is a single word: “Allocate.” In the AI era, ignorance can be an existential issue if not managed from the start. Get full access to The Spiro Circle at www.thespirocircle.com/subscribe

    38 min
  2. The Art of Being a "Disciplined Generalist" in Investing - #0046, Brian Sack

    4 DAYS AGO

    The Art of Being a "Disciplined Generalist" in Investing - #0046, Brian Sack

    For much of the past decade, venture capital has been moving in one direction: specialization. Funds are starting to brand themselves as ‘cyber-only’, ‘fintech-only’, or ‘defensetech-only’, each promising deeper expertise and sharper focus. But in Israel’s startup ecosystem, a counter-trend is growing that favors pattern recognition and intellectual flexibility over narrow vertical obsession. To understand this concept better, I spoke with Brian Sack, a partner at TLV Partners, an Israel-based early-stage venture capital firm. TLV Partners was founded in 2015 and specializes in early-stage investments, particularly in AI infrastructure, cybersecurity, developer tools, and cloud-native systems, as well as vertical AI across industries such as fintech, biotech, healthcare, and more. It has $1B assets under management, and has supported companies such as Next Insurance (acquired by Munich Re), Run:ai (acquired by NVIDIA), Granulate (acquired by Intel), Laminar (acquired by Rubrik), Aqua Security, Aidoc, Qodo, Port, and Quantum Machines, among others. He describes his approach as being a “disciplined generalist,” which he explains as understanding how ideas migrate across sectors. “We want to look at every new technology trend, and we want to look at all verticals across the board,” he said. “We’re just extremely curious people. So we’re always tracking up-and-coming technology trends… Over time, we’ve realized that this has a huge impact as well on our strategy as a fund.” The Spiro Circle is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber. As a journalist myself, I could connect this idea to my own personal attitude of being “a jack of all trades, and master of none”. I often describe my work as needing to cast a wide and shallow net over a variety of industries. But for TLV Partners, they take it a step further - their net is both wide and deep. That philosophy runs against conventional wisdom in today’s VC market, where specialization is often framed as a prerequisite for conviction. But Sack argues that early-stage investing, particularly at seed, demands the opposite: an ability to sit with ambiguity long enough to see connections others miss. “You’re almost sort of like journeying through darkness a lot of the time,” he added. “You don’t have a lot of data, and often you have to make decisions based on intuition or gut feeling. And I think growth investors are great at doing what they do and being very analytical. I prefer, and as a fund, what we like, and what we know how to do best, is to work with founders during the abstract time.” The concept of investing at this early stage was in contrast to a previous conversation I had with a growth investor, who relished in the data and proof of product-market fit. I was fascinated by the difference in approach and how that translated to working with entrepreneurs and navigating markets. “We need our founders to be a little bit crazy,” he added. “They have to have those crazy dreams and visions. I think as a firm, it’s part of our investment strategy and part of our culture, which is why I think a lot of entrepreneurs come to us for investment - because it’s something that is known in the industry that we never think of ourselves as there on the board investing to manage or make decisions on behalf of the company.” You can learn more about the fund in the conversation above. BONUS: Catch the viewpoint of Shay Grinfeld, a growth investor from Greenfield Partners: Get full access to The Spiro Circle at www.thespirocircle.com/subscribe

    51 min

  3. 6 DAYS AGO

    Media narratives in the AI Age - #0045, Hunter Stuart

    In my latest episode, I speak with Hunter Stuart, founder of Big Game PR. Our discussion centered around Hunter’s journey from journalism to public relations, particularly in the context of cybersecurity. Headquartered in Chicago, Big Game PR “brings results-driven public relations and marketing services to B2B technology companies”, including those from Israel. Hunter also shared his experiences as a journalist in Israel, highlighting how living here transformed his understanding of the Israeli-Palestinian conflict. In 2017, he penned an article for JPost that outlined his journey and how his experience here changed his perception of the region and its people. He emphasized the complexity of narratives surrounding this issue and the importance of seeing both sides to foster understanding. We then turned to the evolving landscape of PR and journalism more generally, particularly in the age of social media and AI. Our world is increasingly being framed and controlled in echo chambers that set narratives into motion - and so we spoke about the impact on storytelling and public perception. Some takeaways: * The Israeli-Palestinian conflict is “the mother of all narratives.” * It’s easier for people to craft a satisfying narrative in their heads about the Israeli-Arab conflict. * People are entering an echo chamber and they like what confirms their beliefs. * The rise of AI and automation has made relationships even more important. * Companies need to start owning their own channels. Preview > “Experiencing Israel” Get full access to The Spiro Circle at www.thespirocircle.com/subscribe

    42 min
  4. When Product-Market Fit Is Only the Beginning - #0044, Shay Grinfeld

    2 FEB

    When Product-Market Fit Is Only the Beginning - #0044, Shay Grinfeld

    There is a moment in every startup’s life when imagination eventually gives way to math. I’ve heard this story hundreds of times before. Founders are rewarded for vision and lauded as dreamers. They pitch an idea, raise a Seed round, build their first product, and iterate. As Shay Grinfeld, a General Partner at Greenfield Partners, said, companies repeat this loop “20 or 30 times” until they land on the one product when the penny drops. “‘They said ‘You know what, actually hits a nerve’,” he told me. For this episode, I spoke to Grinfeld about being an early growth investor, and what happens when companies reach their initial targets in revenue: An achievement, of course, but also the beginning of a much harder phase. Growing a Dream into Profit “That’s when we meet them,” Grinfeld says. The point where early momentum must turn into durable growth, usually around Series B and C, optimism alone is no longer enough. Growth investors arrive with a different question: can this company scale its go-to-market strategy once identifying a successful product-market fit, and will it do this faster than the cost of capital? “You have to grow at a cost that is cheaper than the cost of capital,” he told me. “Otherwise, you will not get the funding that will allow you to grow.” According to Grinfeld, what separates founders who push forward from those who sell early, he adds, is not recklessness but “bravery with confidence… and knowledge.” Greenfield Partners was founded in 2016 and invests in early to growth stages in Infrastructure, Vertical Software, and Deep Tech. It has $1 billion in total assets under management after closing a $400 million third fund in 2025. The “7 Pillars of Go-To-Market” One of its strongest areas is structured thinking around go-to-market and company building. Our conversation frequently referenced the “7 Pillars of Go-To-Market”, when Grinfeld describes growth failure as a structural issue rather than one singular mistake. “Every time you fix something, something else breaks naturally,” he says. For example, hiring ahead of the pipeline creates idle sales teams, and scaling leads without customer success can erode retention. The problem is rarely one pillar in isolation. To address this, Greenfield leans heavily into these pillars as concepts: strategy, sales operations, hiring and enablement, lead generation, partnerships, and customer success. The firm has even written playbooks available for founders to glean their insights. The most underappreciated challenge in that phase, he argued, is the gap between product-market fit and what he calls product-market sales fit. “That’s the moment that you think you can actually sell your product at a cost that is cheaper than the cost of capital,” Grinfeld says. It shows up when non-founders can sell, when the pipeline becomes repeatable, and when revenue sees a predictable pattern. “When it actually clicks,” he says, “it’s magic — because you can start compounding it.” A Signal For Leadership In the end, growth comes down to leadership. The founders who make it through the transition are not the ones with the loudest narratives, but the most adaptable mindsets. “Hungry, humble, smart — in that order,” Grinfeld says. You can watch the entire exchange in the video above. Get full access to The Spiro Circle at www.thespirocircle.com/subscribe

    53 min
  5. Inside Cybersecurity’s AI Arms Race - #0043, Itai Tevet

    29 JAN

    Inside Cybersecurity’s AI Arms Race - #0043, Itai Tevet

    The cybersecurity world is grappling with proliferating AI-based attacks, expanding attack surfaces, and surging daily alerts riddled with false positives. With potentially thousands of warnings flooding Security Operations Centers (SOCs) that something could be amiss, the sheer volume creates endless headaches for security teams. It’s the newest cybersecurity nightmare in the AI era. “In cyber, you have this interesting angle where AI doesn’t only disrupt the ‘normal’ industry that everybody is familiar with, but it also disrupts how cyber attackers operate,” said Intezer Co-founder and CEO Itai Tevet. “There’s an arms race of AI not only on the defense side, but also on the offense side. So I think it’s a very interesting dynamic.” Intezer aims to tackle the “ staggering and unmanageable” problem of limited human capacity in cyberspace. As AI empowers bad actors to target enterprises at record scale, the problem isn’t a talent shortage per se, but that the sheer ability of technology will mean humans will never be physically able to catch up with the new threat landscape, including the 97% of false positive alerts that cause distraction and anxiety among overworked teams. The Spiro Circle is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber. The company is part of a growing category of cybersecurity tools that use AI as an extension of human analysts to manage high alert volumes. It develops an AI-powered SOC analyst to investigate security alerts from existing tools and triage them in minutes, automatically resolving false positives and escalating only critical threats. Founded roughly a decade ago but experiencing a surge in activity in 2024/2025, it recently raised $33 million in Series C funding by Norwest Venture Partners, bringing its total to $60 million. Its clients include giants like NVIDIA, Salesforce, MGM Resorts, and others. As technology increases across all industries, AI will become essential for the survival of SOC teams amid rising threats from bad actors, nation-states, and others. According to Tevet, non-adopters could soon become obsolete. And those who embrace the technology won’t be replaced by it, but rather be elevated by it; human roles will no longer be distracted by small-scale attacks, and they will be able to graduate to more superior positions. “From a global perspective, but in my niche, I have a very clear idea of what’s going to happen,” added Tevet. “It all has to do with the nature of the SOC team job, which is going to absolutely change dramatically. Humans will supervise the AI instead of chasing tickets all day long.” You can watch the full exchange in the video above. Get full access to The Spiro Circle at www.thespirocircle.com/subscribe

    42 min
  6. Why Software Is Moving Beyond “Move Fast and Break Things” - #0042, Ben Bernstein

    25 JAN

    Why Software Is Moving Beyond “Move Fast and Break Things” - #0042, Ben Bernstein

    In the early years of tech innovation, software development was driven by a simple cultural assumption that was born in Silicon Valley: that speed equals progress. Entrepreneurs, founders, and developers were encouraged to move fast, experiment freely, and ship continuously. Restraint, social consequences, or legality were often treated as obstacles to overcome or avoid; necessary evils at best, innovation killers at worst. My latest conversation showed me how that era is coming to its end, and that a more conservative movement is growing from the ashes of the Wild Wild West of progress that saw growth encouraged to ignore guardrails or accountability. According to Ben Bernstein, co-founder and CEO of Minimus, the software world is now entering a period of ideological correction, one that closely mirrors what happened with social media and what the LLM era is susceptible to falling into as well. “We identified the problem the first time,” Bernstein says of his first company, Twistlock. “But what was interesting is that we didn’t solve it the first time… Apparently, just identifying the problem is not good enough anymore.” His previous company, Twistlock, is a cloud-native security platform with security and compliance coverage for users, applications, data, and the cloud technology stack. It helps security teams see vulnerabilities created by cloud-native development and containers, but the team realized that visibility alone didn’t stop the explosion of risk. “There are thousands and thousands of issues in every little application,” he said. Bernstein argued that the issue isn’t malicious developers or bad code, but the excess of code that can cause security issues. “The problem isn’t malicious code,” Bernstein says. “It’s unnecessary code.” This realization has driven the philosophy behind Minimus, which builds secure, minimal container images designed to reduce attack surface by design. After Twistlock was acquired by Palo Alto Networks in 2019 for approximately $410 million, Bernstein got to work on his next company: one that would set out to solve the problem identified by his first. Minimus recently announced a whopping $51 million Seed round to “kill” upto 95% of software vulnerabilities by replacing bloated containers with secure, minimal images, slashing risk and development time across the software supply chain. The round was co-led by YL Ventures and Mayfield, with participation from Bernstein, Dima Stopel, and John Morello. But Minimus is less interesting as a product than as a sign of the times: a broader shift in how the industry thinks about freedom and responsibility. In our conversation, we discussed how the past decade has become somewhat of a pendulum swing: In the early 2000s, security and IT teams held tight control, slowing development. Then came cloud, containers, and open source, and the pendulum swung hard in the opposite direction. “Developers got maybe too much freedom,” he says. “And now they see, ‘my God, these are the consequences of what I just did.’” The result is familiar to anyone who followed the arc of social media. Platforms like Facebook, Instagram, and recently X were optimized for engagement first, governance later. Only later did we realize that their push for scale without guardrails produced systemic harm to young people. Bernstein draws the parallel explicitly: “When you get too much freedom, it’s just too much.” What’s changed is who is asking for constraints. “It’s not even the security team asking anymore,” Bernstein notes. “It’s actually the people who want to innovate. This is because developers now spend their time chasing vulnerabilities, patching dependencies, or responding to issues that never should have existed in the first place. “We cannot allocate 50% of our time to just maintain existing software,” Bernstein explained. “Because it actually stifles our innovation.” In this sense, Minimus represents a broader reckoning on what it means to move fast. Ideologically, techies are starting to recognize that speed without structure doesn’t scale. “Velocity can lead to chaos,” Bernstein says. “And chaos is not progress. Chaos is regression.” Just as social media eventually discovered that moderation wasn’t always censorship, software is now discovering that guardrails aren’t necessarily anti-innovation. They are what make innovation sustainable. Get full access to The Spiro Circle at www.thespirocircle.com/subscribe

    43 min
  7. How Noma Security Engineers Culture for Hypergrowth in the AI Era - #0041, Niv Braun

    19 JAN

    How Noma Security Engineers Culture for Hypergrowth in the AI Era - #0041, Niv Braun

    In the AI boom, speed is being celebrated. Funding rounds are closing quickly, teams can double in quarters, and products ship before the market has time to catch its breath. But for Niv Braun, co-founder and CEO of AI security company Noma Security, the real challenge isn’t how fast a company grows, but about it’s what breaks when it does. “One of the biggest challenges in a fast-moving and fast-growing company is how you grow the team very fast and in a way that will be aligned with the great business growth that we see,” Braun told me. “At the same time, keeping the culture.” Noma is better positioned than most to understand this problem. Founded in 2023, the company has already raised $123 million, including a $100 million Series B, and works with some of the world’s largest and most regulated enterprises. But the speed at which the company grows can be detrimental if not managed correctly. “The moment that you move in a quarter from 40 to 70 or 80 people,” Braun added, “it could completely change the dynamic of the company.” When I spoke to Braun, he described culture as being nurtured and defended through this growth, starting with the hiring process. “Sometimes we see the most amazing talents in all areas,” he explained. “But we don’t think that they’re going to be completely aligned with the Noma culture. And this is why we think that it’s not a good fit.” It’s not about ability ot background, but finding pieces that can glue together. “I don’t think that it’s because we are better than them… I just think that there are two different puzzles,” he added. The Cultural Pillars For Success That discipline is built around three cultural pillars. The first is what Braun calls a winning mentality. “Winning mentality is the state of mind,” he says. “They know how, in crunch time, to do the right thing, to take the right decisions under pressure.” The second is radical ownership. “People that take a topic end to end,” Braun said, describing a culture where engineers influence marketing, sales teams shape product strategy, and silos are actively discouraged. The third is an explicitly anti-blame environment. “It’s super collaborative and anti-blaming culture,” he concluded. Without it, Braun believes proactivity collapses, feedback shuts down, and growth becomes fragile. This is particularly visible in how Noma handles failure. “On every POC that we lose,” Braun explained, “there are going to be lesson learning about it. Again, it’s not blaming, but it’s true learning together.” This environment isn’t helped by softening disappointment, either. “We don’t accept it,” he adds. “We make sure that it doesn’t happen, like never, again.” The AI era could see technology resetting or pivoting every few months, and Braun sees culture as one of the few durable advantages left. “This is the only way,” he says, “to scale together with this DNA.” Today, speed may get you noticed, and large funding rounds get you headlines. But as Noma’s growth aims to show, it’s the culture that will determine whether companies survive. Get full access to The Spiro Circle at www.thespirocircle.com/subscribe

    31 min
  8. Why a “Family First” Mentality Strengthens Leadership - #0040, Zack Levine

    15 JAN

    Why a “Family First” Mentality Strengthens Leadership - #0040, Zack Levine

    In the mythology of company leadership, founders are expected to trade stability for scale. Long hours, constant travel, personal sacrifice. Family life is often framed as something to be balanced later, once the company is big enough to afford it. This week, I spoke to Zack Levine from Checkout.com, who tells a different story. Levine leads Checkout.com’s North American and Israel operations and moved to Israel two years ago from the United States. Today, he is preparing to return to the United States, this time to Dallas, Texas, ahead of the birth of his second child, another son. We spoke about family and how he sees it not as a constraint on leadership, but as the condition that makes leadership possible. His recent decision, he explained, was driven less by ambition than by a belief that professional performance depends on personal grounding. “If I feel good about where things are in my family life, in my personal life, my outcomes at work are way better,” he said. “Family comes first for me. Making sure that my wife and my kid are feeling good and happy. That’s the most important. And then from there, I can build the best professional version of myself.” Checkout.com is a fintech company that provides payment processing services for enterprise clients in the media, technology, and e-commerce space. The company is growing fast, with thousands of employees across more than 20 countries. Levine’s role demands constant travel between offices in the United States, Europe, and the Middle East. So when it came to leaving Israel, many elements came into consideration. “I need the security and stability in my personal life in order to create the best work outcomes and for my kids to have a chance to be raised next to their grandparents,” he explained. This proximity to extended family and being in a manageable travel hub were not personal luxuries. They were operational requirements. I found this framing to run counter to how leadership decisions are often discussed. Moves are explained, especially from Israel to North America, as market access opportunities or strategic positioning. The personal lives and the support systems that allow leaders to function rarely make it into public narratives. But our discussion made them explicit. Parenthood, in particular, reshaped his understanding of leadership - something I could understand on a personal level, too. Running a company while navigating young children and distance from family forced a recalibration of priorities. It’s only natural. The lesson I gleaned from our chat is not that every founder should move closer to family, or that ambition should be softened. But it made me think about how performance can depend on the foundations behind the scenes that are rarely visible to outsiders. Offices, travel schedules, and support networks matter as much as strategy decks and growth targets. For Levine, family stability is not something he protects from work. It is what allows the work to function at all. Get full access to The Spiro Circle at www.thespirocircle.com/subscribe

    34 min
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About

Join me as I discuss issues relating to Israel, tech, media, and news. Sometimes with a guest, sometimes solo. www.thespirocircle.com

Information

  • Creator
    James Spiro
  • Years Active
    2025 - 2026
  • Episodes
    48
  • Rating
    Explicit
  • Copyright
    © James Spiro
  • Show Website
    The Spiro Circle