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Building · WhisperitLast page · Iterate Like a Product Doctor (1 month ago)Up at · 04:30

Journal · Latest entry

March 23, 2026 at 11:48 AM

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.

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About

Building products that make legal work faster, clearer, and more human.

I'm building Whisperit, a secure AI workspace for legal teams. I care deeply about product execution, practical AI, and building things that genuinely help people work better. Outside work, I reset by swimming in cold lakes, training, and sauna. I also love hiking in Valais with my family and cooking for friends.

Make the pain go away. Like a doctor.
Build. Listen. Ship. Iterate.
Scale everything. Keep it human.

Full story →Album of my life

Writing

Public notes on building, learning, and shipping.

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Journal · Archive

Handwritten pages, OCR'd and shared one entry at a time.

Private notes captured with pen and paper, digitised through OCR, and published as a running archive on building, technology, and practical AI.

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March 23, 2026 at 11:48 AM/ 3 pages

Iterate Like a Product Doctor

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March 12, 2026 at 10:43 PM/ 3 pages

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.

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March 9, 2026 at 8:47 PM/ 4 pages

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.

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March 8, 2026 at 7:39 PM/ 3 pages

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.

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March 4, 2026 at 10:46 PM/ 2 pages

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.

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March 4, 2026 at 4:15 AM/ 2 pages

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.

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March 3, 2026 at 8:46 PM/ 4 pages

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

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February 28, 2026 at 10:41 PM/ 3 pages

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.

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February 27, 2026 at 8:12 PM/ 2 pages

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.

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February 25, 2026 at 6:57 PM/ 3 pages

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.

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Contact

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If you have a question, an idea, or want to collaborate, send me an email and I will get back to you.

Location: Lausanne, Switzerland
Building: Whisperit ↗
X / Twitter: @romaindewolff ↗
LinkedIn: romaindewolff ↗

Romain de Wolff.

Iterate Like a Product Doctor

Building products that make legal work faster, clearer, and more human.

Public notes on building, learning, and shipping.

What We’re Shipping in Whisperit v3: The AI-Native Legal Operating System for Lawyers

AI for Lawyers: What Actually Changes When You Start Using It Every Day

Voice Dictation for Lawyers: Why More of Them Are Starting by Talking

Secure AI Workspace for Law Firms: Why Another AI Tool Is Not Enough

Handwritten pages, OCR'd and shared one entry at a time.

Iterate Like a Product Doctor

Scale Everything Keep It Human

The Rollercoaster of Building a Startup

AI Is Reshaping Every Part of

Eat Your Own Product

The 4 AM Founder Advantage

Shadow Days Are the Cheat Code

A Day of Doing Nothing

Learning at Impossible Speed

Writing Under Watching Eyes

Talks and conferences where I've shown up.

AI Conference at GJD Lausanne

BrownBag LegalTech with Weblaw

Interview with Swiss LegalTech Association

First Prize at Weblaw Forum 2025

Contact me