The Habit That Made You Successful Is Now Killing Your Company

Jan de Vries · 2026-08-12

What is the one habit that got you here that is quietly killing you right now? I put that question to a room full of founders at the EU-Startups Summit in Malta this May, and I could see it land. Every founder in that room had a habit they were proud of – a personal superpower that closed the early deals, fixed the product, and willed the company into existence. In most cases, that same habit was already working against them. Most founders treat scaling as accumulation: more knowledge, more people, more process. My experience points the other way. The expertise that made you successful yesterday is the very thing that will kill your company tomorrow. Scaling demands the painful, constant work of dismantling what worked yesterday. It means unlearning your best habits – which makes your unlearning velocity your most durable competitive advantage. ### The Scars to Prove It Across every company I have worked at, the same pattern repeated: the habit we were proudest of became the thing we had to let go of. Facebook was built around B2C growth and direct performance advertising. The founder was deeply involved in every product detail. Once past $1.1 billion in revenue, that model hit a wall. The company had to build a genuine B2B product and sales organization – a completely different set of capabilities – while simultaneously navigating the platform shift from desktop to mobile, one of the most radical transitions in its history. How the product was developed, how it was sold, and how the organization was structured all had to be rebuilt. Airbnb's early model ran on scrappy local field teams, which were essential for building trust in a platform nobody believed in yet. It worked brilliantly, until it stopped scaling. The company centralized for global efficiency, then later had to rebuild local sales capability as it expanded to serve professional hosts. Two reversals, each requiring the leadership team to walk away from the approach that had demonstrably worked. Deliveroo felt like joining a different company every few months, because it was. We went from survival mode, with a small group making decisions on pure instinct after the company came close to bankruptcy, to hypergrowth of 2x in 18 months, which required a decentralized organization that trusted local teams to drive growth. Then, as the market demanded profitability, we had to unlearn hypergrowth itself in favor of operational efficiency and sustainable growth. Three companies, one lesson: at every stage, be ready to abandon the thing that made you. ### What Breaks, and When Between $9.7 million and $28.1 million ARR, the founder is the bottleneck. At around 150 people you can no longer know every employee, and the tribal knowledge and informal alignment that powered the early years simply break. There are too many deals for you to be the hero in all of them. The unlearning here is dismantling the "founder-as-the-OS" model – passing the baton on actual decision rights rather than just delegating tasks. You have to replace the chaotic energy of the hustle with a Minimum Viable Operating System: regular planning cycles, clear KPIs, and systems that work when you aren't in the room. When you scale to $28.1 million and $94 million ARR, the danger goes underwater. Your dashboard can look perfectly healthy while the company drowns in siloed teams, misaligned roles, and decisions that take weeks instead of hours. The visible metrics sit above the waterline; the real problems such as decision rights, internal systems, culture sit below it. The unlearning here is resisting the instinct to fix things by changing targets or pushing the team harder. When a team breaks at this stage, the cause is almost always below the waterline. Fixing the business requires two distinct operational shifts. On one hand, explicitly defining not just what you will do but also what you will stop doing is essential for execution velocity. ### The Unlearning Playbook Here's what I've learned about making unlearning practical rather than theoretical: - **Schedule deliberate abandonment reviews.** Every quarter, ask: "What did we do last quarter that we should stop doing now?" Make it a formal agenda item, not a casual thought. - **Hire for adaptability, not just expertise.** The perfect candidate for your next stage might look nothing like the perfect candidate for your current stage. - **Create a "kill criteria" for every initiative.** Define upfront what would make you abandon a project. This removes the ego from the decision later. > "The most dangerous words in business are 'we've always done it this way.'" – The sooner you internalize that, the faster you'll scale. ### The Bottom Line Your unlearning velocity is the one metric that predicts whether you'll survive the transition from scrappy startup to sustainable company. The founders who thrive aren't the ones with the most knowledge – they're the ones most willing to shed what they know. So ask yourself: what habit are you most proud of right now? Because that's likely the first one you'll need to unlearn.