“Where there's pain and there's no technology, there's opportunity”: James Ding's path from Palantir engineer to legal tech innovator

Every conversation I have with James reaffirms why we invested in DraftWise. His thoughtful pauses and carefully chosen words reflect a mind that's always calculating, always refining. This meticulous approach isn't just a personal trait; it's the driving force behind DraftWise, the AI-powered legal tech startup he co-founded and scaled impressive heights in just four years.

James embodies the rare combination of visionary thinking and execution excellence, a blend that transforms bold ideas into groundbreaking realities in the complex world of legal technology.

From global law firms like Mishcon de Reya and Orrick as clients to revolutionizing how lawyers work, DraftWise's rapid ascent mirrors James's own journey from Palantir engineer to innovative founder. In our recent conversation, we explored this transition, the intricacies of understanding customers, and the common misconceptions in the increasingly crowded legal tech space.

James’ journey from Palantir to DraftWise illustrates the crossroads many top engineers face: choosing between pushing technological boundaries and creating real-world impact through entrepreneurship.

At Palantir, James was at the center of working on some of the hardest tech problems, leading large-scale efforts and contributing to open-source systems. This experience proved to be the perfect training ground for his entrepreneurial journey.

 "At Palantir, I was given exposure and opportunity to do more than just build products," James recalls. "We didn't have a sales team, nor did we have a marketing team. So effectively, you had to sell it yourself or work with people who weren't salespeople to sell it."

Yet, he found himself yearning for something more.

"Starting a company was a way to take control of my destiny," James explains. "To choose the problems I wanted to solve, and how to solve them."

This shift highlights a crucial trade-off: while engineering offers the thrill of solving complex technical puzzles, entrepreneurship provides a unique opportunity to directly shape technology's impact on people's lives. It's a balance between depth and breadth, between technical excellence and real-world application.

For James, the desire to create tangible change won out. "I wanted to see more of a direct impact of technology on people and why exactly my work mattered," he says. This drive for impact became the foundation of DraftWise, leading James to discover a satisfaction that pure engineering, despite its intellectual rewards, could never fully provide.

James didn't embark on this journey alone. He joined forces with his Palantir colleague Emre Ozen, now DraftWise's CTO, who brought expertise in product and data management, and Ozan Yalti, now CSO, a Stanford Law graduate who contributed a decade of legal practice experience. This combination of deep tech knowledge and industry expertise positioned the team uniquely to tackle the challenges of legal tech.

James and his co-founders didn’t set out with a plan to disrupt legal tech. "We didn't think we were going to start in legal tech. It wasn't the first space we looked into," he recalls. Their decision was driven by identifying a real pain point. 

They conducted interviews with almost 100 lawyers, and what they heard was consistent across the board. "Almost every lawyer told us the same thing – they work long hours, their lives are consumed by their work, and it can be tempting to leave the firm."

This level of dissatisfaction made it clear to James that they had found an opportunity. "Where there's pain and there's no technology, there's an opportunity," he reflects.

A critical factor in DraftWise's success is James's relentless focus on truly understanding the customer. From my experience, this ability to extract meaningful customer insights is a hallmark of successful seed-stage companies—it often distinguishes those that scale from those that falter.

While many founders take user feedback at face value, James approaches it with a deeper level of scrutiny.

"There’s a lot our users tell us they want, but there are so many biases in play," he explains. "They’re trying to please you, and they also have an optimistic bias."

"Instead of asking for opinions, we ask for facts about real experiences," he says, probing with questions like, "Tell me about the last time you encountered this problem," or "How long ago did it happen?"—focusing on specifics rather than hypotheticals.

This level of dedication to understanding user behavior is exactly what sets apart the startups that successfully grow beyond the earliest stages. 

James continues: "We don’t just rely on interviews; we sit next to our users, observing how they work, what software they use, and where their pain points are."

This immersive, almost ethnographic approach to user research allows DraftWise to develop solutions tailored to real-world problems, not just perceived issues, a crucial element that separates successful startups from those that fall short.

DraftWise's success in addressing pressing needs for its users in the legal industry also stems from James' nuanced understanding of the industry's diversity. This is crucial and often overlooked, leading to significant misallocation of capital in the legal tech space.

"The incentives between a law firm and an in-house legal team are pretty different," James explains, "and the incentives between a big law firm and a small law firm are pretty different."

He points out that even within law firms, different specialties have unique needs. "An M&A lawyer does very different work to a private equity lawyer, and different again from a real estate lawyer," he adds.

This nuanced view is something that outsiders, including many investors, tend to misunderstand about the legal tech industry. The result? A flood of capital into solutions that fail to recognize these distinctions. The AI hype gave a new boost to legal tech startups, but underneath the excitement around AI, a lack of sophistication will leave many new startups struggling to meet a real need for clients or help them solve meaningful problems.

As James observes, "Startups build amazing niche technology using LLMs for a set of users, but then realize their user base is too small for venture-scale returns, so they pivot to target all legal practitioners indiscriminately." 

This broad-brush approach, often driven by pressure for rapid scaling, is precisely why so much money is flowing in the wrong direction in legal tech.

This is not, James feels, an approach that will yield good results. 

“I'm skeptical of startups that think they can sell to all of the legal industry out of the gate. The fundamental thing that everyone's missing, especially these companies responding to VC capital and the VCs themselves is that, at the end of the day, these are very different businesses that happen to be in the same field.”

Given how thoughtful James is about his industry, it's easy to forget that he is still early in his entrepreneurial career - DraftWise is less than five years old.

What has helped James handle this transition from engineering to being a founder and a leader? Some of the most helpful elements of the mindset go back further than his professional experience.

"I was a competitive athlete for a long time and much of the leadership team at DraftWise have been competitive athletes.” This experience, he says, taught him "the value of delayed gratification and sticking to a process even when it doesn't yield immediate results."

This patience and long-term thinking are critical in the legal tech space, where changes don't happen overnight and building trust with conservative law firms takes time.

It is also an approach that is built into our own philosophy at Bek Ventures: if you want to succeed as a founder or as an investor and achieve long-term sustainable success - a rarity in VC - you need to have discipline, be willing to delay gratification and focus on building lasting value.

James’ vision for DraftWise is ambitious yet focused, "I want DraftWise to be the software people open every day when they start work. Like a Microsoft Outlook or a Microsoft Excel - it's just necessary." But his impact extends far beyond a single product or company.

James’ journey exemplifies a broader shift in the tech industry towards more thoughtful, user-centric innovation. In an era of quick exits and rapid scaling, James and DraftWise remind us of the enduring value of patient capital and sustainable growth. They challenge us to think not just about what technology can do, but how it can fundamentally improve professional work and life.

As we look to the future of legal tech and beyond, the true product innovators will be those who, like James, can bridge the gap between cutting-edge technology and real-world needs. They'll understand that lasting change often comes not just from disruption, but from deep understanding and patient evolution.