The Spiro Circle

Susanne Senoff recalls a time early in her security career when a former colleague would insist that meetings take place in his office. But the office was papered with lewd materials.HR let it stand, she recalled, because he was so good. “That would never happen now,” said Senoff, now CISO at Conga.Her point wasn't that the problem was solved. Senoff was speaking alongside two founders, Shahar Bahat of Pluto Security and Yael Fraiman of Predict Security, who described a different barrier: fewer overt acts and more assumptions.Fraiman said women interviewing at startups still worry about whether to disclose that they have children. Her friends debate how much to share about their private lives: “Should I share that I’m married?”Bahat described the funding version. Before she began raising capital, she recalled how someone once advised her that she would be better off “showing up without a ring.” In our conversation, she said she ignored the advice: “I did raise money with a ring because I don’t want it to be a matter.”The companies they are building address different aspects of workplace security. Bahat’s Pluto Security helps businesses monitor and secure the AI tools, agents, and applications employees use and build. It recently announced $42 million in total funding, $34 million of which was a Series A round in October. Fraiman’s Predict Security focuses on insider risk, analyzing activity across company data, applications, and AI tools to distinguish ordinary work from potentially harmful behavior. Both are portfolio companies of AlphaDrive, a venture capital firm founded by Yaron Elad and Elik Etzion focused on cybersecurity and AI. Its AlphaDrive Wisdom network brings practicing CISOs into investment evaluation and company development, where members contribute personal capital and advise founders on products, customer needs, and commercial strategy. Senoff co-leads that community alongside her role at Conga, connecting the three participants through both investment and practitioner support.My first three-guest studio panel on The Spiro Circle brought together women from different generations and professional backgrounds, with overlapping experiences of assumptions about their gender.What the data showsIsraeli data suggest the drop-off of women in top roles across leadership positions happens after entry, not before it. Women represent about 34% of Startup Nation employees, a share that has remained largely unchanged for three decades. For younger cohorts, it is slightly more equal. Women aged 25-34 are 39.5% of employees, against 31.5% at ages 45-54. In cybersecurity, data put women at 26.3% of non-managerial employees, 15.5% of senior executives, and 5.1% of CEOs at companies founded from 2013 through 2024.In other words, women are already underrepresented before entering the industry, but their representation is lower still in senior leadership.The times are changing“We’ve been resilient,” said Senoff, adding that female CISOs have “just ignored our gender, in a way.” A better approach was asking whether they were good at the job. To her board, the question of gender doesn’t come up. Senoff said her board’s concern was how secure the company was, rather than her gender. But for younger women, it does, and she mentors them. “We just want to be celebrated for just being good at our jobs, not because we’re a woman who’s good at our jobs.”Senoff offered a card-game metaphor: being a woman is one card, and it’s an Ace. It can be an advantage or hindrance since it can claim both high and low values. Bahat expressed a similar pragmatism: “As a founder, you use whatever you have.” Before starting Pluto, she said that hearing other women discuss both the challenges and advantages of building companies helped her see a clear path and pursue it in her own way.For founders, investors, and buyers, the practical question is where assumptions bite: interviews, fundraising, or sales - all moments with financial consequences. But the shift they describe, from visible conduct to unspoken assumptions, is harder to measure and, on their account, harder to see.[Preview: “That’s a very male point of view”: Women techies push back against my questions] Get full access to The Spiro Circle at www.thespirocircle.com/subscribe

Building The Spiro Circle has made me think differently about what gives a media business its value. When Omri Hurwitz returned to the show, we discussed a reversal I find fascinating: how institutions that once dismissed podcasting are now investing heavily in it.Major media companies and investors are buying themselves into the studio. Traditional outlets are embracing the format on their own shows, trying to compete for the eyes of millions who tune in each week to hear their favorite podcaster. I asked him what this trend tells us, and why a form of media that was disregarded is suddenly worth real money.His answer was a chain of three links, and I haven’t heard it put more simply. “It’s eyeballs, podcasts, brand capital, [then] institutional capital.” If Alex Cooper’s podcast is bigger than a CNN segment, then brands would want to advertise on Alex Cooper’s podcast. And once the brands are there, “then institutionals would want to buy equity or something inside that podcast,” he explained.In his view, it’s audience first, then advertisers, then owners. And if that’s the order, it means the audience isn’t a byproduct of the deal. It’s the asset.One major deal of this kind was Spotify’s reported $200 million licensing deal for The Joe Rogan Experience, renewed in 2024 and again in 2026, each at an estimated $250 million. In April, OpenAI acquired the daily tech show TBPN, which will report to its chief global affairs officer. Meanwhile in Europe, ETN, a TBPN-style daily show, raised a $1.6 million seed round and moved to a five-day-a-week schedule. Companies, brands, and investors are following the same logic: find the room where people already show up, then buy in.The audience is the assetWhat caught my attention more than the valuations was what he said about creators. “They can monetize with brands. They can monetize with institutions. They can monetize directly to subscribers.” Three doors, and you can walk through any of them, or all three. It certainly gave me some good ideas as I continue to grow my show, The Spiro Circle, beyond an essay newsletter into a podcast and conference publication. And it made me consider the type of audience I’m cultivating: Techies interested in Israel, cyber, or geopolitics. Omri suggested that if you want to live on subscribers, you need to go broad; if an audience is niche, subscribers may not pay the bills, but institutions may agree to fund the venture. You don’t need a million people. You need the right few who care about the thing you cover.I’m biased here, because it’s why I did what I did. After five years at a traditional newsroom, I wanted room to explore a broader range of stories and develop my own editorial voice. Building The Spiro Circle has given me that opportunity, alongside the reporting I continue to do for other publications. Many journalists are following the same route.Omri’s enthusiasm for the possibilities facing independent creators resonated with me. “You have so many options today to be a creator,” he said, and I think he’s right. Investment brings responsibilityBut here’s where I want to be careful, and where I pushed back against Omri’s argument a bit. More doors means more people who can pay you, so long as your audience is aware of who is covering the cost. I am quick to disclose if my show is produced with the help of collaborators like Forbes, or if there is any perceived conflict of interest among guests, businesses, and myself.For a lot of the time, subscribers provide the funding - but when that bleeds into brands, sponsorships, or investors, then owners mean someone eventually has an interest in what gets said. For millions of people listening to Joe Rogan before an election, or watching a tech show funded by the makers of ChatGPT, it can become difficult to identify the difference between journalism, PR, and marketing. My view is that audiences should be able to distinguish independent reporting, sponsored work, and commercial partnerships. Relevant payments and ownership interests should be visible, and the boundaries around editorial control should be clear. A disclosure gives readers information they need; the work itself must still earn their trust.Omri predicts that media ownership will become a decisive advantage for PR firms. He has built his own business around that model, which gives him both experience of it and a financial stake in its success.For me, the opportunity comes with a responsibility. I want to build a publication that people value enough to support, and that partners see a reason to back. Its credibility will depend on clear disclosures, editorial independence, and a willingness to correct mistakes.The audience may be what attracts the investment. Its trust is what I need to keep earning.[PREVIEW: Why legacy media wants a seat in the podcast studio] Get full access to The Spiro Circle at www.thespirocircle.com/subscribe

Arona Maskil told me about a client whose chatbot could answer in 27 languages. Despite this, she recalled the client saying it still had not figured out “how to give feedback to our team in India without causing offense.” It captures a gap I suspect many of us have fallen into: translating a message is not the same as understanding how it will land.Maskil has spent more than 25 years in cross-cultural work and advises global teams through her firm, Training CQ. Her book, Reading the Room Across Borders: Leading Effectively Across Cultures and Markets, argues that cross-border deals and teams usually stumble on interpretation, not on talent or intent. Her BRIDGE model breaks the friction into six dimensions, and we cover it in our conversation: * Building relationships * Risk-taking* Interactions * Decision-making * Group dynamics * EngagementOne part of our conversation stayed with me: how AI changes our responsibility to communicate across cultures.The message gets better. Does the understanding?Think about how many of us use AI now: we draft emails to colleagues or customers in another country, to soften a piece of criticism, or prepare for an international meeting. AI results are usually polished, grammatical, and confident. But that polish can ignore what the sender may need to know about the person receiving it.“It can translate the words, but it still cannot read the room,” she said.Models may have access to public information or correspondence history, offering clues about previous disagreements or the recipient’s role. Even with access to correspondence, a model may lack important context. And a smooth draft makes those gaps easy to overlook, or irrelevant, once people actually meet in person and get a better sense of one another. That idea raises a tension I want to examine: does outsourcing the wording tempt us to skip the work of understanding the relationship? It seems worth asking since more people rush to prompt a draft response in seconds without considering the broader consequence.AI’s default voice isn’t neutralResearchers have started measuring this. A 2024 PNAS Nexus study compared five OpenAI models’ answers with nationally representative survey data and found their values resembled those of English-speaking and Protestant European countries. In newer models, specifying a cultural identity in the prompt improved alignment for 71%-81% of countries and territories (though not for all of them). The study tested particular models using values-survey questions; it did not assess whether AI-written workplace messages were understood as intended.It still helps explain why fluent, apparently neutral output deserves scrutiny. Choices about directness, deference, and self-expression carry assumptions, and smooth prose makes them harder to see. The study suggested “using cultural prompting and ongoing evaluation to reduce cultural bias in the output of generative AI.”Maskil makes the same point from the consulting side. AI “tends to treat the cultural norms as a neutral benchmark,” she said. Unless you tell it otherwise, “it’s gonna write it with your own cultural glasses.”So AI can respond to cultural context, and the research suggests the same. The harder question is how accurately that context describes the actual situation.The trouble with “making it Japanese”Maskil’s own example is telling an AI “this email is for my Japanese colleague.” That gives the model additional context. But in doing so, it can also invite a generic profile potentially leaning into stereotypes.“National culture gives us tendencies. It gives us an overview, but they’re not absolutes; they’re not rules,” she explained. And while Maskil used national comparisons, such as Israelis being direct and the Japanese being highly risk-averse, she warned against applying them to individuals.That made sense: National patterns are where you can start, but the person across the table still needs their own unique treatment. It’s not something AI can do on its own - we still need to be ‘in the room’ to fill social cues that an algorithm can overlook, such as eye contact or posture, among others.What stays with usA chatbot that can answer in 27 languages is powerful. But reliance on AI to help us communicate may mean that sometimes our messages fall on deaf (or unprogrammed) ears.AI doesn’t remove our responsibility to stay culturally aware, something even harder to do as the world settles into workflows relying on virtual screens, generated summaries, or automations. It can make it easier to forget that we still need to check the output and to confirm that we’ve been understood. A better-written message should prompt us to ask two questions: Have I been understood as intended, and have I understood the other person?For transparency: Arona provided a copy of the book. I received no payment for this coverage and have no financial interest in its sales.[5-minute preview: The BRIDGE flow model: Six dimensions of cross-cultural business] Get full access to The Spiro Circle at www.thespirocircle.com/subscribe

In Greek mythology, a mortal king of Corinth, Sisyphus, was condemned by the gods to roll a boulder up a hill, only to watch it roll back down each time. For eternity. The punishment was not the labor itself, but the absence of an end point. No finish line, endgame, or closure. Jonathan Langer, co-founder and CEO of Act Security, argues that the image fits much of modern cloud security. Security teams work through an ever-growing list of findings, including vulnerabilities, misconfigurations, and risky settings, one item at a time. “Nobody ever finishes the list,” Langer told me. “That’s the dirty little secret in cybersecurity.”His company has built its brand around this, even including the message “don’t be a Sisyphus.” When we spoke, I wanted to understand whether that was simply a memorable metaphor - or a useful way of thinking about an industry that keeps finding more work for itself.Langer’s thinking about this began at Medigate, the medical-device security company he previously co-founded. Its technology could show customers what devices they had and the risks associated with them. But customers eventually asked a fairly obvious question: Now what? The dashboard problem“Now I know. Now I have all this risk. Now I have all these issues and findings. What do I do with it?” he recalled them asking. The idea with Act is to reduce the access that makes attacks possible, including permissions that allow an application or person to reach systems they do not need.The problem was documented long before today’s AI boom. Palo Alto Networks’ Unit 42 analyzed more than 680,000 identities across 18,000 cloud accounts for its 2022 research. It found that 99% of the cloud users, roles, services, and resources examined had excessive permissions left unused for at least 60 days. (That measures identities with excessive permissions, rather than the proportion of all permissions going unused.)Langer’s approach rests on a premise that an attacker needs access to enter an environment, move through it, and extract data. In cloud environments, permissions granted at deployment tend to persist because teams fear that removing them will break applications. Narrowing an over-broad permission at its source can resolve many findings at once, rather than one ticket per symptom. Act Security was founded in 2025 and left stealth this summer. It has raised $60 million, comprising a $20 million seed round led by Team8 and Bessemer, and a $40 million Series A led by Notable Capital. And it is selling a solution to this problem.Unused does not mean unnecessaryThe obvious challenge here is that unused access does not immediately label it as unnecessary. Some permissions exist for emergencies or infrequent operations. Langer said Act tries to reconstruct a developer’s original intent from documentation, tickets, observed traffic, and code scanning, and removes only access that exceeds it. It also checks new deployments to prevent excessive permissions from returning. Without that second step, cleaning up existing access would simply begin another cycle.As with most cybersecurity solutions, the margin for error is narrow. Even a 90% success rate, he said, would mean disrupting production in the remaining 10% of cases, which he called unacceptable. He described the target as “five nines,” or 99.999% accuracy. This is an aspiration - Langer did not cite customer results during our conversation.Will the permissions return? Understanding an organization well enough to change its permissions safely requires more than recognizing that something has been idle. Recent AI incidents in the news underline why those boundaries remain important. Langer remains optimistic that better controls can contain most attacks, even if cybersecurity problems cannot disappear completely. “This world that we live in, physics still applies. If there is no access between one sandbox and another, or a sandbox to the internet… and we use strong deterministic controls, even if you have the smartest AI out there, it cannot defy the laws of physics.”Cybersecurity may never have a finish line. But that does not mean every task should repeat indefinitely. The test is whether removing unnecessary access today leaves an organization harder to attack tomorrow, without disrupting the work those permissions were meant to support.[Note: In the recording, I mistakenly referred to Sisyphus as a god. He is a mortal king of Corinth]The Spiro Circle is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.[Preview: Why Act Security built its brand around Greek mythology] Get full access to The Spiro Circle at www.thespirocircle.com/subscribe

Three years after October 7, the conversation about antisemitism reaches far beyond the immediate aftermath of the attacks. It touches universities, political movements, foreign funding, and the everyday decisions Jews make about belonging. This week, I spoke with Charles Asher Small about how those all connect, and what he believes institutions and Jewish communities should do next.Small leads the Institute for the Study of Global Antisemitism and Policy (ISGAP). He described its ambition to connect academic research with public policy, and our conversation followed that path: from a broad diagnosis of democratic fragmentation to questions about evidence, university leadership, and Jewish identity.His opening argument was that antisemitism thrives amid wider social and institutional weaknesses. He described the extreme left, extreme right, and radical political Islam as different forces attacking the democratic centre. In his analysis, hostility towards Jews provides a point of convergence between movements that otherwise have little in common.Foreign influence and the institutions shaping opinionThat led us to ‘strategic entryism’, the term his team uses to describe ideological influence entering established institutions. Small focused on the Muslim Brotherhood and Qatar, arguing that funding and networks can advance the movement’s ideas within Western universities and cultural life, something I have covered separately at JNS. He sees universities as especially consequential because they educate future journalists, professors, and political leaders.He argues that the financial pressure faced by universities makes them more receptive to outside money, while the ideas circulating within them eventually reach wider society - a serious allegation about institutional influence.“If you think of what happened at universities on October the 8th, 2023, this to me is a watershed moment where people, I think, were shocked,” he said. “But this has been sort of in the works for decades.”I wanted to understand how his team measures the impact of the funding it identifies, beyond pointing to protests or shifts in rhetoric. He cited ISGAP’s 2023 “Networks of Hate” report, saying universities receiving Qatari funds had “300% more instances of antisemitism” than those that did not, although he acknowledged the difficulty of scientifically proving the broader ideological relationship he described. The exchange raised an essential question: how do we establish what money changes, as well as where it goes?Criticism, antisemitism, and the question of belongingWe also discussed his concerns about propaganda and social media. While the central focus of ISGAP has been the Muslim Brotherhood and Qatar, Small described Iran, Russia, and China as contributing to an environment that fragments Western societies through infiltration and propaganda, including the use of bots.It was here I wanted to challenge him. Universities have long been places of protest, and I believe Israel’s government is as open to criticism as any other. So where does legitimate political opposition end, and antisemitism begin?“We have to define antisemitism in a scientific, comprehensive manner that allows for criticism,” he said, accepting that Israeli policies can be criticized. But institutions must also recognize rhetoric and movements that dehumanize Jews. Later, he spoke about Jewish families questioning whether they could remain in countries where they had lived for generations (something I have written about before), and framed this vulnerability as a warning about the condition of democratic citizenship.The new Hebrew University-European Forum Barometer offers a passing echo of those concerns: Israeli respondents overwhelmingly viewed Israel as safer for Jews than Europe, while Jewish Israelis reported strengthened Israeli identity. Those are perceptions, rather than a test of Small’s explanations, but they show how immediate questions of safety and belonging have become.When I asked what he would do as a university president, Small’s answer began with education. Students should study democratic principles and understand their responsibilities as citizens, he argued.“To live in a democratic society, every generation has a choice.”We discussed greater transparency around foreign university funding and ISGAP’s efforts to turn research into policy through the DETERRENT Act, a congressional bill designed to increase oversight and lower reporting thresholds for foreign gifts and contracts at colleges and universities that receive federal student aid. The House of Representatives passed the bill in March 2025, and it has been referred to the Senate. “Jewish Consciousness” and life after October 7The conversation's final turn came when Small described ISGAP’s Jewish Consciousness framework, which draws parallels from South Africa’s anti-apartheid movement and the influence of Black Consciousness.He argued that we Jews should define ourselves by drawing on our own traditions, knowledge, and history rather than accepting labels imposed onto us by hostile outsiders. I raised what I called “the hijacking of history”: How Israel’s critics exploit language associated traditionally with Jewish persecution, and apply it against Jews themselves. “One of the things that we need to do is define ourselves based on our terms,” he replied.That thought brought the episode’s different strands together. Small’s proposed response combines research, institutional accountability, democratic education, and a deeper understanding of Jewish identity. Our conversation moved between what others say about Jews and what Jews can say about themselves. Three years ago, questions were urgent and immediate: security, safety, who was funding what. This episode suggests those questions remain, but have evolved beyond how institutions should respond to antisemitism, toward who gets to define what being Jewish even means while that fight continues.[Preview: “Strategic Entryism”: How Qatar’s money entered America’s universities] Get full access to The Spiro Circle at www.thespirocircle.com/subscribe

There was a moment in my latest conversation with startup psychologist Yael Daniely that surprised me. She described someone who walked into her clinic and asked to keep his laptop open so that Claude could run live for the entire session.“He came with Claude to the room and asked to keep Claude open because he must be in contact with Claude and give him [updates]… because Claude is working and he must be reactive to him. Otherwise Claude will be stuck.”She said no. “It wasn’t easy for him to close the laptops slowly, slowly.” He couldn’t understand why, in that moment between founder and therapist, the chatbot needed to be left at the door. It’s a funny image, but it speaks to something much larger happening among founders in tech. Yael Daniely has spent years researching the psychology of the individual founder, but also the relationship between co-founders and, interestingly, the relationship between a founder and their family spouse. Over her career, she has helped individuals and pairs work through trauma, anxiety, financial concerns, and (increasingly) the impact that AI has on their roles and identity.She described that moment in her office as a symptom of something bigger than one dependent client. AI isn’t just changing how founders build companies; it’s becoming a relationship for some of them. “Everyone says that their best friend now is ChatGPT... they can share all their dreams, secrets, fears, and emotional burdens and issues with their partner with ChatGPT.”Daniely is not dismissive of AI as a source of support. She said a conversation with a chatbot in the middle of a sleepless night may help someone calm down, and that some tools can complement therapy. Her concerns are placed in founders who put too much emphasis on a responsive machine that can supply everything a person needs from a relationship.“They cannot completely take over the connection and the relationship that’s happening in the room with the therapist,” she said.AI has entered the chat The intense capital around these technologies is mirroring the emotions. Global startup funding hit $506 billion in the first half of 2026, the biggest half-year in venture capital history, with AI startups accounting for around 77% of all that investment. Three companies (OpenAI, Anthropic, and xAI) that build addictive chatbots were behind $237 billion of that total.Against this backdrop, the impact of AI is actually two-fold. Not only are founders forming attachments to their AI tools, but they’re also watching the technology overhaul the entire process of work, causing them to develop existential questions surrounding self-worth and identity. For CTOs, she said, the shift has triggered something closer to professional grief. She shared how some feel they are losing their profession, which they connect to a sense of self. For CEOs, it triggers an anxiety if they see a competitor raise funds quickly, and interpret that news as evidence that they are too slow, too old, or building the wrong thing.Daniely doesn’t think the answer is rejecting the tools; rather, monitoring “how you control AI versus AI controlling you.”But that founder who couldn’t close his laptop is the extreme version of a very ordinary 2026 problem: tools designed to make founders faster are starting to make some of them feel like they’re already behind, all while making it easier to swap human connection for an algorithmic companion.Including, it turns out, inside the therapy room.You can connect with Yael Daniely on LinkedIn and check out more of her work here: https://yaeldaniely.com/[Watch a preview: The Founder, the Therapist... and Claude?] Get full access to The Spiro Circle at www.thespirocircle.com/subscribe

I recorded a conversation yesterday with Alexander Piskunov, a government AI advisor and founding partner at KAAN Ventures, at a strange little intersection of timing. UN Secretary-General António Guterres had just used his address to call for a multilateral AI risk framework. Sam Altman and Dario Amodei were preparing to appear before the Security Council. And President Trump, predictably, was telling the room that the US had no interest in slowing down.Eventually, the Security Council session happened - specifically because it felt AI’s security implications weren’t getting enough attention.Yoshua Bengio, who co-chairs the UN’s scientific panel on AI and is considered a “Godfather of AI”, went first and told council members the dangers posed by advanced AI are “real and imminent.” Amodei warned that AI could become a risk to humanity itself, while Altman pushed for shared global benchmarks to measure AI capabilities and the safeguards companies claim to have in place. I asked Piskunov the obvious question: does America actually have the leverage to just ignore all of this?“It’s still quite important to separate rhetoric from the actual steps that would be made,” he replied. It made much of what is happening at the UN this week sound less like policy and more like theater. Effective theater for some, perhaps, but theater nonetheless.Piskunov is the founding partner of KAAN Ventures, where he's spent the past decade backing deep-tech investments across the US, Europe, and Southeast Asia. More recently, he's shifted into advising governments (Pakistan, South Africa, Kazakhstan, South Korea, among them) on how to build an AI strategy from a position that isn't the US or China.He doesn’t think Trump’s refusal to engage is dangerous or ignorant, as many believe. He thinks his position makes strategic sense, given the shape of the game governments are playing. “The AI race is a game where if you lose your first place, it’s almost impossible to catch up given how rapidly everything is developing,” he explained. If that’s true, then every voluntary slowdown is a gift to whoever doesn’t slow down. And if calls for the US to slow AI development don’t apply to China, is that who we want to win and lead this revolution? As for a potential third place: The EU used to be a contender, but he points out that “the EU is just too over-regulated right now” to remain a key player, and its national champions can’t compete on data or scale anymore.Rather than simply staying out of the conversation around AI regulation this week, President Trump went the other direction completely - as is so often the case. "The United States also totally rejects any attempt to construct a globalist scheme to control for the artificial intelligence being spoken of so much now," Trump said (adding that he thinks AI should be referred to instead as ‘superintelligence’ or ‘SI’).Which brings us to the paradox that started this whole conversation. The same tech executives publicly warning about AI risk and pitching Trump for guardrails are, in Piskunov’s words, making “a very cynical case.” They understand their own limitations more intimately than they let on, and they know that if they can’t out-innovate their competitors, their next best move is to get those competitors regulated. Safety concern and competitive strategy, in other words, aren’t necessarily different things. Piskunov thinks the real value lies in the psychological fight, not the race to regulate. Discussions happening this week “open up the Overton window” for the public and show that governments are taking the risk seriously, even if nothing binding follows just yet. And that may be enough for Guterres or Bengio for now.The week will end with Trump meeting with Xi in Washington - his first visit since 2015. In an act of goodwill, US Treasury Secretary Scott Bessent announced that the two countries will extend their trade truce to January, set to originally expire in November. Perhaps they’re saving this bigger fight for later.America’s current position isn’t just a rejection of multilateral concern about AI. It sees voluntary restraint or an international framework as a move guaranteed to lose against those unwilling to restrain themselves. And so far, no one in New York can argue otherwise. You can connect with Alexander on LinkedIn here: https://www.linkedin.com/in/alexander-piskunov/ The Spiro Circle is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.[Catch a preview: Is Trump Right to Ignore the UN on AI? This Advisor Says Yes] Get full access to The Spiro Circle at www.thespirocircle.com/subscribe

Uzi Krieger has jumped from planes, descended into underwater caves, and skied slopes steep enough to unsettle most people’s stomachs.When I asked what draws him to it, he put it down to a philosophy he lives by. “I think it’s a theme in life of being a little bit of an explorer,” he told me. “I don’t want to say ‘living on the edge’, but trying to see how far you can go, how hard you can push, and do it in a very structured way.”For Krieger, now General Manager of Cloud Security and Exposure Management at CrowdStrike, risk is not about recklessness. “It’s not just about jumping off a cliff or diving hundreds of feet underwater,” he explained. “It’s more about taking on a challenge and trying to see how far you can get… That’s how I’ve approached extreme sports, or work, or almost everything I do in life.”The idea of “structured risk” is interesting to me. I learned it personally at a young age when obtaining my SCUBA license: Plan your dive, dive your plan, I was told. It’s something that also grounds my decisions as I grow my independent media venture after departing from corporate newsrooms last year.Krieger was the right person to speak to about this idea and how he applied it across his career. He started in corporate America’s telecom sector, running a business unit inside a large, publicly traded company, until he left to pursue something else. “Very early on I realized that moving fast and being able to get really good results is something that can only happen in Startup World,” he explained, which is also what attracted him to Israel’s startup ecosystem. He went on to found and run several companies, most notably Reposify, an external attack surface management company which CrowdStrike acquired in 2022. CrowdStrike's leadership asked him to help bring more “founder DNA, startup DNA” into the organization.Krieger credited the mentors of his early startup years with teaching him that line between risk and recklessness. “They had a very unique combination of very strong conviction and an extreme, structured, almost scientific way of how you get to being successful,” he told me. It comes down to preparation, not appetite: “You want to take risk, but it’s not just any risk. Where’s the passion? Are you really all in? What is the plan? Are you actually building a plan, or are you just trying to wing it?”The new speed of risk That same instinct now shapes how CrowdStrike approaches its own market, which has hit $243.3 billion, and a stock price circling within distance of an all-time high. Exposure management, which is the practice of identifying and prioritizing an organization’s most exploitable weaknesses, was largely a background chore before AI adoption pushed it into boardrooms. “It’s no longer a question of ‘why do we need this,’” Krieger said of the shift. “It’s ‘how do we move 10 times faster? How can we be ahead of the curve?’” This mindset gets him safely out of a cave, or back on the ground with both feet, and it’s what separates a security strategy from a scramble. But it requires work. “You really need to build that muscle. It’s not natural. People are risk-averse, but how do you transform risk aversion into something that allows you to take risks, enjoy the journey, and do it in a way that you become successful?” His question stayed with me until long after our meeting.The AI era is asking everyone to take risks. Company pivots, career changes, market shakeups… all of them will require us to make decisions or take actions that will impact our personal and professional lives. “It boils down to basic human nature and being a good person. People want to do good; people want to be successful. It doesn’t matter if it’s in a small company or a big company,” he concluded. “I think [it’s about] not losing the edge that you have with a startup, and taking that into a larger organization, and bringing that impact.”[Watch a preview: Why this CrowdStrike manager skydives, cave dives, and calls it “Structured Risk”] Get full access to The Spiro Circle at www.thespirocircle.com/subscribe

Well, here it is: Episode 100 of The Spiro Circle. When I recorded the first episode 18 months ago, I had a rough idea of what this show could be. I wanted it to be a place where long-form conversations about Israeli tech, geopolitics, or society could get broader attention. Now, with a growing audience across 20 countries and partnerships with international media channels like Forbes, I am proud to see what it is becoming, and that these conversations are getting the attention they deserve. Startup Nation yearned for long-form English conversation, and I am pleased to be helping fill that missing gap. For the 100th, I brought in Nitay Milner, co-founder and CEO of Orion Security, and Emily Fontaine, Global Head of Venture Capital at IBM Ventures, to talk about why every major company should rebuild its data security strategy in this AI era. I find it fitting that our conversation on how a large corporate company saw potential in a scrappy Israeli startup was positioned as the 100th episode. Thanks to all who have joined to share their stories so far, and thank you to all those who keep tuning in.Onwards to 200. - JSThe data loss prevention industry has organized itself around a relatively stable threat model.A disgruntled employee may copy files to a USB drive. Or a phishing attack could expose credentials to an outside attacker. Maybe someone accidentally CCs the wrong person on an email with sensitive information. Solutions focused on perimeter controls or policy rules were imperfect, but understandable when the threats were often caused by humans.But that model is no longer sufficient. According to research by Cyberhaven Labs, whose 2026 AI Adoption and Risk Report analyzed data movements across 222 companies, nearly 40% of all AI interactions now involve sensitive data, with the average employee inputting proprietary information into an AI tool once every three days. Threats don’t disagree insofar as they disaggregate, accelerate, and, in some new cases, remove the human from the equation entirely.Nitay Milner, co-founder and CEO of Orion Security, offered a framework for understanding how the landscape has changed. In a recent episode with Emily Fontaine, Vice President and Global Head of Venture Capital at IBM, which backed ORION’s $32 million Series A in February 2026, he described the three categories of traditional data leakage that the DLP industry was built to address: human error, malicious insider activity, and external attackers. “[Perhaps] I accidentally did ‘Emily@IBC’ and not ‘IBM’,” he said, by way of illustration, “and sent the entire board deck to the wrong person. That happens a lot. I call it keeping honest people honest.” The second category, he noted, involves deliberate exfiltration, what he called the “Snowden” scenario. The third involved external actors penetrating an organization and quietly siphoning data over time.Milner co-founded Orion Security in 2024 with CTO Jonathan Kreiner. It aims to replace traditional DLP (data loss prevention) tools with an automated, context-driven platform. Using LLMs and specialized AI agents, the platform continuously detects and analyzes data loss indicators in real time, capturing context for content sensitivity, data lineage, user identity, behavioral intent, and environmental purpose.New anatomies, new leaks Traditional categories of DLP remain relevant, of course. But Milner identified two new vectors that are reshaping the problem. The first is data extraction into third-party AI: employees uploading sensitive documents like earnings calls, customer records, or source code to unmanaged AI platforms before those materials are cleared for external use. “Taking the earnings call, which is super sensitive data, before the earnings call report was published, and uploading it to like an unmanaged ChatGPT or Claude,” he said. “It’s very, very sensitive, and data is now in the hands of a third party that you don’t have any agreement with.”The second vector is data exfiltration not by humans at all, but by AI agents operating inside the enterprise. “AI agents doing human work inside the organization, having access to super sensitive data,” Milner explained. “Think about an AI agent email assistant that has access to your Google Drive, takes the entire customer list and sends it to the wrong person. That’s data exfiltration by AI.”The scale of this emerging risk is becoming measurable. According to a 2026 Cloud Security Alliance report, 82% of organizations already have AI agents operating in production environments, while only 17% enforce runtime access controls consistently across those deployments. A separate finding from Proofpoint’s 2025 Data Security Landscape report found that 32% of organizations identify unsupervised data access by AI agents as a critical threat.Fontaine framed the underlying problem as one of movement, not just volume. “Data is a huge asset that must be protected, more so than ever before,” she added. “It’s moving across clouds, it’s moving across applications, agents, ecosystems. It’s moving across so much more than it was ever before. And we have to make sure it’s secure, that it is governed correctly.”IBM Ventures, the strategic investment arm of IBM led by Fontaine, operates a $500 million fund focused on AI and quantum technologies — and its bet on Milner and the team reflects IBM’s belief that the arrival of large language models has fundamentally broken the assumptions on which traditional data security was built, creating entirely new leakage paths that legacy DLP tools cannot detect.A new era for DLPThat governance challenge is exactly what today’s DLP industry is no longer built to handle. Policy-based systems depend on known patterns, like a credit card number matching a regex or a file name triggering a rule. They cannot, by design, interpret context or whether a particular data movement constitutes a legitimate business action or an exfiltration event. Milner’s breakdown offers enterprises a useful starting point to identify which of the five categories (legacy or AI-era) represents the highest unaddressed exposure in a given environment, and build from there. “Understand your organization,” he concluded. “Based on this real data, get to decisions, train your employees, and help them understand how to use data safely.”[5-minute preview: Is your AI leaking company secrets? IBM & Orion Security explain] Get full access to The Spiro Circle at www.thespirocircle.com/subscribe

For two decades, the winning formula in consumer tech was simple: maximize time on screen. Last month that formula got a multibillion-dollar price tag attached to it when Meta agreed to pay roughly $17 billion to settle a multistate lawsuit alleging Facebook and Instagram were deliberately engineered to be addictive to teenagers.Now, one Israeli investor thinks the backlash could create an opening for a very different kind of consumer product, and for a new generation of Israeli founders.Oren Charnoff is the Co-founder and a General Partner at Sticker Ventures, a Tel Aviv early-stage fund that invests exclusively in Israeli B2C startups. He sees the settlement as validation of a thesis his fund was already investing behind, based on changing consumer habits among young people. “We want to find more companies whose goal is not to increase time spent on the app,” he said. “We hope to see more ‘IRL’ things being built by Israelis.”He points to two U.S. examples he admires. The first, Tin Can, is a landline-style phone that plugs into the wall, paired with an app that lets parents approve who their kids can call; Charnoff says it’s doing roughly $80 million in annualized revenue. The second is Board, a digital game console built entirely around in-person play. “The only way that you can interact with it is with another person with you,” he said. Closer to Sticker’s own market, Charnoff cites Edikted, the Israeli-founded Gen Z fashion label, which The Wall Street Journal recently reported as achieving roughly $460 million in revenue: “They crush it on retail. They crush it for offline discovery.”Startup Nation’s advantage in the changing marketThe shift makes it perfect timing for Israel’s tech DNA to tap into adapting markets. Startup Nation has accumulated decades of expertise in adtech, gaming, fintech and cybersecurity, producing a generation of founders trained to measure, test and optimize. Add to that a new type of internet-native, young immigrant to Israel who is a product of globalization, and those skills can be unleashed on the world’s biggest GDP category: consumers.“The same quants who do anomaly detection in cyber can optimize the budget, channel and yield of consumer growth,” Charnoff said. He traces the lineage directly to Israel’s earlier tech waves. “Adtech is one of the founding mothers and fathers of B2C,” he said, pointing to the exodus of former ironSource employees now building consumer companies of their own. The craving to steer away from online apps and toward “In Real Life” extends into dating apps, both in his portfolio’s orbit and out of it. Companies are moving away from “unlimited swipes whose goal is to maximize dwell time” toward an AI concierge model that delivers one or two curated introductions a week, rather than an endless feed of profiles. According to Charnoff, 38% of Sticker Ventures’ deployed capital sits in the Health & Wellness category - framing the appeal generationally: millennials were “an experiment of unlimited internet access”, he told me, while Gen Z is driving “a huge trend to get back into IRL... experiences.”Charnoff and Sticker Ventures aren’t betting that the attention-economy giants disappear. But the “hipster move” into B2C investments is placing new bets on the next generation of consumer winners built for the time people spend away from their news feeds, not the time they spend scrolling through it.“B2C’s been a big part of Israel’s ecosystem for a long time,” he concluded, listing success stories like Waze, Oddity, Superplay, eToro, Wix, Simply, MyHeritage, and others. “We’ve always been doing this… I just think with AI, there’s a renewed interest to do it… It’s just way more attractive to be a B2C entrepreneur now.” [Preview: Why building B2C in Israel is suddenly a "hipster move"] Get full access to The Spiro Circle at www.thespirocircle.com/subscribe