Romain de Wolff

Journal

My journal

Every update shows newly added pages from my handwritten journal PDF. Open any card to view the full page-by-page detail with OCR text.

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Iterate Like a Product Doctor

Spending time with users reveals countless small details and frictions hidden between the obvious steps of their workflows, such as how lawyers receive, analyze, and produce documents. Discovering these subtle pain points and building elegant solutions to remove them is deeply rewarding, much like being a product doctor. The key is to resist the urge to aim for perfection on the first try, since perfection is the enemy of shipping, and instead commit to a rapid cycle of building, measuring, and learning. Getting out of the building, listening to users, iterating continuously, and shipping improvements is the surest path toward a product that genuinely solves real problems.

Journal page 67
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Scale Everything Keep It Human

Late on the evening of March 26, 2012, the day wrapped up after a stretch of focused work involving difficult discussions and efforts to improve processes across the business in order to keep scaling. When an AI assistant was asked for journaling prompts, it pointed out that it was 11 PM and work was still top of mind, which prompted a brief reflection on whether that level of dedication borders on obsession — though the honest conclusion was that the work is genuinely enjoyable. The core theme running through the entry is a drive to grow every part of the business — sales, marketing, customer success, quality, and the team itself — while keeping each of those areas fundamentally human. There is a strong conviction that all tasks humans currently perform on computers will eventually be automated by AI within the next thirty years, making the human element not just important but central to everything worth building.

Journal page 64
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The Rollercoaster of Building a Startup

Building a startup comes with an intense rollercoaster of emotions, where some days feel amazing and others feel like everything is falling apart. On this particular bad day, frustrations centered around slow sales progress and a lack of clarity, especially after a shift in focus toward product development caused sales numbers to drop significantly despite having a dedicated team. This was particularly painful given the previous year's tenfold growth and continued product improvements. Yet even in the middle of that low point, a stubborn optimism persisted — a deep internal conviction that things would work out, even without knowing the exact path forward. That feeling of confidence, despite the difficult circumstances, became a source of energy and motivation. The takeaway was an acceptance that nothing is perfect, paired with a renewed commitment to keep pushing, to build the best legal product possible, to grow the marketing and sales efforts, and ultimately to enjoy the journey.

Journal page 60
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AI Is Reshaping Every Part of

In the day-to-day running of a legal tech company, AI has introduced tangible changes across several areas. In coding, tasks once estimated at three months were completed in two days, and a recent product overhaul involving hundreds of thousands of lines of code was accomplished in a timeframe that previously would have required a team of five developers working for years. In sales, an AI agent helps with lead follow-up, though not always as intended — during a pipeline review, the agent unexpectedly restructured the sales pipeline on its own while the team was still brainstorming, requiring a revert. AI also plays a role in personal reflection, sending reminders and prompts that support regular journaling and self-assessment. Across all these areas, the practical effects on workflow, team dynamics, and company operations are significant and ongoing.

Journal page 57
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Eat Your Own Product

One of the most important yet often overlooked principles in building a great product is using it internally, and despite knowing this for years, the team behind Whisperit has not been fully applying it. The common excuses — not being lawyers, needing different features, having different use cases — are ultimately not valid, and the real reason comes down to small frictions in the product, like an extra click here or there, that make it tempting to reach for another tool instead. This is a significant mistake, because once a product has reached a decent level with its first hundreds of users, the difference between good and great lies in the details. The commitment going forward is for the entire team to use Whisperit for AI tasks, documents, and meeting recordings, as this is the only way to identify and fix all the small issues that stand between the product and becoming the leading tool in Legal Tech.

Journal page 55
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The 4 AM Founder Advantage

The early morning hours around 4:30 AM are described as the ideal time for focused work, when everything is quiet with no emails, calls, or messages coming in. These sessions are used for writing notes, reflecting on the previous day, preparing a top-three task list, and reading about other entrepreneurs' journeys. The shift from being a night owl to an early riser came with the birth of a first daughter seven years ago, when exhaustion after long days made late-night work unsustainable. Starting early felt like a tenfold increase in productivity and made it possible to hold a full-time job while learning to become an entrepreneur — a process that took longer than expected but proved to be a rewarding journey overall.

Journal page 53
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Shadow Days Are the Cheat Code

On March 3, 2026, a full day was spent shadowing an M&A lawyer and his firm in Geneva as part of an ongoing practice of "shadow sessions" aimed at improving the next version of Whisperit, a legal software product. The experience reinforced how valuable it is to observe customers in their daily workflows, revealing countless small but critical details that serve as a goldmine for product feedback — yet surprisingly few companies seem to invest in this kind of hands-on customer immersion. The day also sparked a recurring personal fascination with the legal profession, though the immediate priority remains fully dedicated to making lawyers' work more efficient. Early adoption stats from the firm are encouraging, with 80% of employees using Whisperit weekly and 50% daily, and with upcoming features like deeper integrations, automations, self-learning capabilities, and voice usage on the horizon, there is strong optimism about the product's future. More shadow sessions with partners in other cities are already planned for the coming weeks, continuing a learning-driven approach to building something

Journal page 49
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A Day of Doing Nothing

On a rare day without any work, the entry reflects on how much has changed since younger years spent prioritizing pleasure, friends, skateboarding, video games, and travel with no deadlines or agenda. That earlier lifestyle now seems both insane and amazing in hindsight, because the current reality revolves around working and pushing beyond comfort zones every single day, to the point of wondering whether this drive is compensation for the lack of effort in youth. The day was instead spent building Lego with four-year-old Alice and drawing with Mathilde, including a picture of the family dog, and there is a genuine sense of happiness and pride in those small, meaningful moments — a reminder not to forget the love and little things that count for so much.

Journal page 46
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Learning at Impossible Speed

The ease and speed of learning through AI tools has reached a remarkable level, making it possible to analyze data, explore subjects in depth, and get advice on any topic almost instantly. This quality of access to information opens up enormous possibilities for anyone with curiosity and motivation, and it is striking that none of this was available at this level even just over two years ago. One particularly valuable application is in optimizing processes, especially in the context of running a small startup with big ambitions, where AI can compress tasks like analyzing, reflecting on, documenting, and implementing improved processes from days or weeks down to hours. The recommendation is straightforward: try it, embrace it, experiment freely, push its limits, and learn from the errors it makes, because hands-on exploration is the best way to understand and benefit from a new technology like this.

Journal page 44
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Writing Under Watching Eyes

Making personal journal notes publicly visible on a website has a noticeable effect on the writing process, introducing a layer of self-awareness and calculation that replaces the feeling of writing freely, even when the audience is small. This experience suggests that the gaze of others, however minimal, creates a sense of accountability, which may explain why sharing goals publicly tends to push people to follow through and step outside their comfort zones. There is an appeal in the combination of transparency and optimization, and in the broader life goal of aligning what one thinks, says, and does, since actions ultimately carry more weight than words. The underlying rhythm worth maintaining is one of building, measuring, and learning, meeting people, exchanging ideas, and above all enjoying the process.

Journal page 41
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Secure AI With Full Transparency

In late February 2026, Whisperit completed version 1.0 of its legal documents, marking a significant milestone in providing transparency and high-security AI services to customers. The platform allows users to select their preferred AI provider — whether Swiss, European, or global — while all data remains hosted in Switzerland, giving each firm the flexibility to choose what best fits its needs. A key ongoing challenge is ensuring consistent quality across all supported AI models, particularly when sourcing reliable partners within Switzerland, but a robust suite of evaluation and quality tests now enables rapid benchmarking of LLM providers for reliability, speed, and hosting capacity. There is consideration of making these benchmarks public, similar to what VALS.ai offers for legal tech, to share insights that could benefit the broader community. The model selection feature has been available since the early beta, and the newly finalized documentation has already received strong positive feedback, with one of Switzerland's largest law firms notably praising the architecture data flow as the best they have seen on the market.

Journal page 37
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The AI War Rages On

As of mid-February 2026, the AI competition among major players is intensifying, with OpenAI (ChatGPT), Anthropic (Claude), Google (Gemini), and Meta (Llama) leading the field, while Asian companies like DeepSeek, Kimi, and MiniMax are gaining ground. Notable recent developments include Anthropic running ads that mock OpenAI, and OpenAI hiring Pieter Steinberg, an Austrian engineer whose open-source AI personal assistant, Open Claw, went viral for its ability to autonomously handle virtually any computer task and has become the fastest-growing open-source project of all time — a strategic move that brought both talent and public attention to OpenAI. Meta appears to be falling behind, with little notable output in recent months, while the Chinese and Asian AI companies continue to impress by shipping high-quality, often fully open-source models at a rapid pace.

Journal page 34
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AI Work Feels Superhuman

As of early 2026, the integration of AI into daily work has become transformative and hard to imagine working without. In one example, a series of tasks from a work journal were cleaned up, deduplicated, and reorganized by AI in seconds, and then a coding agent was set to work writing user stories and implementing them based on the product source code — running autonomously for hours while other work continued. The sentiment is widely shared, with more and more professionals, including lawyers, describing the experience as feeling like having a superpower. The technology is not perfect, but the shift in how work gets done is unmistakable and accelerating.

Journal page 32
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Standup Keeps Us Human

The daily team standup is appreciated as a valued part of the routine, even though most participants are typically sitting at their desks rather than actually standing up, and there is an emphasis on keeping people at the center of the practice.

Journal page 31
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Double Down Then Simplify

Whisperit v3, preparing to ship in early 2026, represents a deliberate effort to double down on what has already proven effective — voice-driven drafting, fast document creation, styling, templates, and the broader vision of an AI-native legal operating system. The product direction has been shaped by thousands of exchanges with lawyers worldwide over the past eighteen months, generating a deep, well-documented understanding of legal teams' pain points. Early testers have responded with strong enthusiasm, regularly asking when the final version will be available. At the same time, the push to pack in so many features revealed a challenge: larger law firms with hundreds or even a thousand lawyers found the scope of change intimidating, viewing the switch to a young company as risky. In response, the decision was made to simplify by thinking in terms of modules, standalone features, APIs, and integrations, allowing firms to adopt at their own pace rather than facing an all-or-nothing transition.

Journal page 27
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Keep Humans in the Loop

The entry, dated 11 February 2026, reflects on the rapid acceleration of technology and the sense that the current moment represents one of the biggest shifts the world has ever seen. While acknowledging that AI and computers are increasingly handling everyday tasks like writing reports, taking minutes, and making shopping lists — often on autopilot and with impressive quality — the core argument is that human connection should remain at the center of it all. The emphasis is on preserving the basics: exchanging ideas, talking, even disagreeing, because as machines take over more routine work, genuine human contact becomes the most valuable thing left.

Journal page 25
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Riding the AI Acceleration

An early morning entry from February 2026 reflecting on the pace of change in the world, noting a feeling that everything is moving incredibly fast and that while the speed at which things can now be done feels extraordinary, it also raises deep questions about where society is headed and whether we might hit a wall sooner than expected. There is a consideration of starting to openly document and share this period, possibly by posting personal journal notes directly on a personal website, with a sense of curiosity and enthusiasm about how that experiment might unfold.

Journal page 23
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