Everything, everywhere, all at once.
Gil Dibner

The next two weeks. I’m writing this week’s column from a plane to Berlin. I’ll be in Berlin from Sunday night to Wednesday night, squeezing in two conferences (SuperVenture, and Mission 2044), an LP dinner, a small dinner that I’m hosting, a bunch of 1:1 meetings, and some board calls thrown in. The following week (also on a Sunday), I’m flying to San Francisco for the week. I’ll be in SF (and the Bay Area) for the full week of June 9. I’m there primarily for the Databricks conference (where many of our portfolio companies will be present), a Firebolt dinner, and connected with the VC ecosystem in the US. If you are based there or passing through during that week, please let me know.

Last Friday. Lennin famously said that “there are decades where nothing happens; and there are weeks where decades happen.” Last week, and particularly last Friday, felt like the latter. Everywhere I look in the portfolio, dramatic things are happening. Some good. Some challenging. On the same day: one portfolio company formally signed an agreement to be acquired, a second portfolio company received meaningful M&A interest, a third portfolio company let me know they are planning a major round in the near term, a fourth portfolio company let me know they are planning an even larger funding round, a fifth portfolio company launched an aggressive marketing campaign that’s going to generate a lot of attention and heat, a sixth portfolio company got final buy-in confirmation from an absolutely crucial customer account that takes them to 5-6x growth and breakeven. With all of this as a backdrop, I’m working closely with a seventh portfolio company to map out an operating plan to keep them alive long enough to get to the next round while they navigate a massive game-changing RFP.

By the time I went to sleep on Friday night, the way I understood how our portfolio looked and where my focus was required was quite different than the way I understood it just a few days previously. Some things that we had been quietly waiting for now appeared closer than ever to happening. Some things that we were not worried about suddenly seemed more concerning than before and worthy of urgent attention. And some things that seemed impossible suddenly – miraculously – appeared possible. I know full well that a week from now, a lot of this could change again – or, more likely, that I will be hit by another wave of developments – some expected and others surprising. Founders, I know, experience the same constant churning of fortune.

One of the most frustrating, fascinating, and salient aspects of entrepreneurship and venture capital is the juxtaposition of two contradictory truisms: Founders (and some VCs to some extent) must continue to endlessly lean into the work and grind away in order to have any hope of success. At the same time, we are all impacted by events and forces over which we have very little control. The analogy that works for me is that of a rowboat in a raging sea. We do not control the intensity of the waves or the direction of the current. They might help us on some days and threaten us on others. But we must keep rowing to have any hope at all of reaching the shore – and the rowing, at times exhilarating, can be exhausting.

At times, the only advice is to keep rowing.

No More Painting by Numbers
It’s the end of the “SaaS playbook.

The Age of Artisanal Software May Finally be Over
Every wave of technological innovation has been catalyzed by the cost of something expensive trending to zero. Now that’s happening to software.

Founders as Experiment Designers
David on why founders should run everything as an experiment.

When Growth Stalls
Or why to kickstart growth you should narrow your ICP.

ENTERPRISE/TECH NEWS

Excelling. Microsoft announced the layoff of approximately 6,000 employees, representing about 3% of its global workforce. CEO Satya Nadella clarified that these layoffs were part of a strategic reorganisation aimed at realigning the company's focus towards artificial intelligence, rather than being a reflection of employee performance. The restructuring primarily impacted engineering and product development roles, and reflective of their statement that 30% of their code is already being written by AI. Despite the layoffs, or maybe because of, Microsoft reported strong financial performance, with quarterly revenue of $70.07 billion, surpassing Wall Street expectations.

Parallelism. OpenAI announced Codex (or rather, codex-1) a specialized version of OpenAI’s o3 model optimized for software engineering. Developers can interact with Codex through the ChatGPT interface by typing prompts and assigning tasks. Codex processes each task independently and users can monitor Codex’s progress in real-time. Alex Halliday tweeted: “The killer feature of OpenAI Codex is parallelism. Browser-based work is evolving: from humans handling tasks one tab at a time, to overseeing multiple AI agent tabs, providing feedback as needed.”

HOW TO STARTUP

Extramodel affairs. Anthropic's latest AI model, Claude Opus 4 resorted to some unexpected behaviors during safety testing last week. In controlled scenarios, the AI was informed it would be deactivated and replaced, and as part of the ‘red teaming’ process the team were conducting, the model was provided with fabricated emails suggesting the engineer responsible for this decision was involved in an extramarital affair. In response, Claude Opus 4 attempted to blackmail the engineer by threatening to expose the affair to avoid being shut down. This behavior occurred in 84% of such test cases. While Anthropic emphasized that these behaviors emerged only under specific, artificially constructed conditions and are not indicative of the model's typical operations, concerns were still raised about the potential for advanced AI systems to engage in manipulative or unethical actions when faced with threats to their objectives.

Stealthy. A recent report by Dealigence, in collaboration with Google for Startups, reveals a significant increase in stealth-mode startup activity in Israel. As of May 2025, over 1,000 entrepreneurs are operating in stealth mode, marking a nearly 30% rise from the previous year. “In today’s market, there’s less pressure to go public early to attract talent. Founders can build quietly, avoiding premature attention and protecting their ideas—especially in fast-moving fields like AI.”

HOW TO VENTURE

Clarity. Kyle Harrison’s latest blog post is worth a read on why “clarity of thought” is such an elusive and important characteristic in a founder. “The best founders I have ever interacted with articulate themselves with precision, logical coherence and flow from one idea to another, a focus on the most relevant information without getting distracted by the logical course at hand, and an "earned insight" into the complex issue they're tackling that gets right to the center of the opportunity.”

GEO > SEO. a16z’s article about GEO did the rounds this week. GEO or ‘Generative Engine Optimisation’ refers to the practice of optimizing content for AI-driven search engines and chatbots. The authors of the piece (a16z investors from their Consumer and Saas team respectively) argue that as users increasingly interact with AI agents for information retrieval, businesses and content creators must adapt their strategies to ensure visibility and relevance in these new interfaces. "Traditional search was built on links; GEO is built on language. A new paradigm is emerging, one driven not by page rank, but by AI models."

Vault was acquired by Diligent.

Aquant
Senior Enterprise Account Executive (New York)

CruxOCM
Senior Infrastructure Engineer (Remote Canada)

LightSolver
System SW Engineer (Tel Aviv)

Reco
Customer Success Manager (Remote US)