Author: Sivan Kadosh

Why Churn Spikes After Early Growth (And How to Stop the Bleeding)

January 26, 2026 • 9 min read

A few years ago, I advised a promising startup that had just crossed the $5M ARR mark and entered the ‘Hyper-Growth’ phase. On paper, everything looked incredible: a successful raise, dozens of new hires, and shiny new offices. But if you haven’t lived through this transition, it’s hard to grasp the hidden costs of rapid […]

Read more

The Paradox of Success: Why Discovery Dies After Product-Market Fit

January 22, 2026 • 9 min read

The ability of startups to find Product-Market Fit lies in their very definition: they are, quite simply, startups. This isn’t just wordplay. As Steve Blank famously noted in the Harvard Business Review, a startup is a temporary organization designed to search for a business model, not just execute one. It is an agile learning machine […]

Read more

The Founder Bottleneck: Why the Visionary Becomes the Velocity Killer (And How to Scale Out of It)

January 21, 2026 • 9 min read

In the early days of a startup, the founder is the ultimate “compression engine.” You hold the market insights, the customer pain points, the technical constraints, and the strategic vision in a single brain. Decisions are made at the speed of thought. This “Founder Telepathy” is your greatest competitive advantage; it allows for the rapid […]

Read more

Why Feature Velocity Hides Product Failure (And How to Fix the Engine)

January 20, 2026 • 7 min read

There is one trait I believe every Product Manager must possess to consider themselves truly great: the ability to look in the mirror and say, “I was wrong.” As a young PM, I spent years confusing motion with progress. We would ship features at a breakneck pace without moving the company an inch toward a […]

Read more

The Chasm of Complexity: Why Roadmaps Stop Working at 20-50 Employees

January 14, 2026 • 9 min read

In the early days of a startup, the “product roadmap” is usually a shared hallucination between the founder and the first two engineers. It exists in Slack snippets, late-night Zoom calls, and perhaps a chaotic Trello board. Communication is high-bandwidth, and the distance between a customer request and a code commit is measured in hours. […]

Read more

Why Product Strategy Breaks After Series A (And How to Fix the Engine)

January 12, 2026 • 9 min read

Physics teaches us a simple truth about gravity: it’s relative. On Earth, an average person weighs about 75kg. But if you take that same person to Jupiter, the immense gravity creates a crushing weight of nearly 190kg. This is exactly what happens when a startup crosses the threshold from Seed to Series A. Suddenly, everything […]

Read more

Crossing the Chasm to Enterprise: Why Your SMB Roadmap Will Fail Big Clients

January 7, 2026 • 7 min read

You just lost a $100k contract. The demo went perfectly. The champion loved the interface. The ROI case was undeniable. You even agreed on the pricing. Then, the deal was handed off to the “IT Security Review,” and it died a quiet, suffocating death. Why? Not because your AI isn’t smart enough. Not because your […]

Read more

The Hostage Situation: Why Non-Technical CEOs Need a CPO to Challenge Engineering

January 6, 2026 • 7 min read

Your CTO looks across the table and sighs. “The legacy code is a mess. We can’t build that feature until we do a total rewrite of the backend. It will take six months.” Your Lead Developer chimes in on Zoom. “Actually, that specific request is technically impossible with our current stack. The API doesn’t support […]

Read more

The Series B Trap: Why VCs Are Passing (Even If You Hit Your Revenue Targets)

December 30, 2025 • 7 min read

You hit your revenue targets. You grew 2.5x year-over-year. You have a polished pitch deck and a pipeline full of logos. Yet, for the third time this month, a Series B partner has told you, “We love the vision, but we’re going to pass right now.” Welcome to the Series B Trap. In the zero-interest […]

Read more

Your “AI Strategy” is Just a Feature Wrapper (And Investors Know It)

December 29, 2025 • 8 min read

Your board is demanding an AI moat. Your competitors are shouting about “Agentic Workflows” on LinkedIn. And your engineering team just spent three weeks pasting an OpenAI API key into a chat window to launch a “chat-with-your-data” feature. That is not a strategy. It is a feature wrapper. In 2024, you could get away with […]

Read more