Some careers follow a carefully planned path. Others unfold unexpectedly, shaped by chance, curiosity, and moments of quiet courage. Deepthi Rajeev’s journey into law belongs firmly to the latter.
Today, as the Founder of DRN Legal, she stands at the intersection of law, technology, and business, helping companies navigate some of the most complex and evolving legal questions of our time. But her story begins far from boardrooms and regulatory debates.
An Unplanned Beginning That Found Its Purpose
Deepthi did not set out to become a lawyer. A science student with engineering aspirations, she chose law almost on a whim, sparked by a casual conversation. That decision led her to the prestigious National Law School of India University, where her understanding of law expanded far beyond courtroom dramas and pop culture perceptions.
Like many students from middle-class backgrounds, practicality shaped her early decisions. With an education loan to repay, corporate law seemed like a stable and promising path. Her ambition was clear: to secure a role at a top-tier law firm.
She achieved that goal when she joined the Mumbai office of Amarchand & Mangaldas (now Cyril Amarchand Mangaldas). But what followed was not the clarity she had hoped for.
When the Dream Doesn’t Fit
Assigned initially to capital markets and later to regulatory work, Deepthi found herself struggling, not with capability, but with alignment. The work felt distant, the environment intense, and the experience, at times, overwhelming.
It was a phase marked by self-doubt. Was corporate law really the right path?
In hindsight, she recognizes that it wasn’t just the work, it was also the environment. High pressure, tight timelines, and difficult interactions can often cloud one’s sense of purpose.
So, she did something many hesitate to do: she walked away.
Reinvention Through Risk
Her next move was anything but predictable. She relocated to Bangalore and joined the TMT (Telecom, Media, and Technology) team at Trilegal, despite having no prior experience in the field.
It was a leap of faith, and it paid off.
For the first time, she found herself genuinely engaged. Advising technology companies, particularly on how to design products in compliance with evolving laws, brought together problem-solving, creativity, and real-world impact. The supportive environment and intellectually stimulating work helped her rediscover her confidence.
This phase marked a turning point. Law was no longer just a profession; it became a tool to shape innovation.
From Advisor to Builder
Eight years into her career, Deepthi faced another defining choice: continue the law firm track toward partnership or explore something new.
Curiosity led her in-house.
At a very early stage of the startup, Xflow, she stepped into the role of General Counsel. The company was building cross-border payment infrastructure in a highly regulated and evolving space, without even having a live product at the time.
It was a challenge that required her to start from scratch.
Working closely with teams, partner banks, and regulators, she learned the nuances of fintech, cross-border compliance, and regulatory frameworks. More importantly, she experienced something transformative, being embedded within a business. This gave her a perspective that traditional law firm roles often lack. She could now see firsthand how legal decisions influence product design, growth strategies, and risk appetite.
Four years later, as Xflow grew into a Series A-backed company, Deepthi continued to remain part of its journey, now as external General Counsel.
The Birth of DRN Legal
This blend of law firm discipline and in-house experience sparked a larger idea. Deepthi recognized a gap in the way legal services were traditionally delivered, often reactive, fragmented, and disconnected from business realities. She envisioned a model where legal would not just respond to problems, but actively help build businesses.
That vision took shape as DRN Legal.
Her firm reflects a new approach, one that combines legal expertise with business context, aiming to provide solutions that are not just technically sound but practically meaningful.
Navigating the Uncertainty of AI and Intellectual Property
In today’s technology-driven world, Deepthi identifies intellectual property as one of the most complex and rapidly evolving domains.
The rise of artificial intelligence has introduced questions that traditional laws struggle to answer. For instance, if software is generated using AI-assisted tools, does it qualify for copyright protection? Since copyright law typically recognizes human authorship, this creates a grey area for businesses relying on AI-generated code.
Similarly, the widespread practice of scraping data to train AI models raises fundamental questions about ownership and infringement. While processes like text and data mining may not directly constitute copying, techniques like retrieval-augmented generation could blur the lines by reproducing content.
Adding to this complexity is India’s lack of a dedicated statutory framework for trade secrets. Businesses are often forced to rely on contracts and common law remedies, which may not provide sufficient protection, especially in cases involving third-party misuse or data breaches.
For Deepthi, these gaps are not just legal issues; they are business risks that require thoughtful, forward-looking solutions.
Copyright in the Age of Code and Creativity
Copyright, once associated primarily with creative industries, now cuts across sectors, from media and gaming to SaaS and technology platforms.
One of the most common yet overlooked challenges is ownership. Companies often assume they own the work created by employees or contractors, but legally, ownership follows authorship unless explicitly assigned through contracts.
In a world where software forms the backbone of businesses, such gaps can have serious consequences.
Deepthi emphasizes the importance of clarity through well-drafted agreements, careful review of open-source licenses, and proactive risk assessment during due diligence.
The emergence of AI adds another layer of complexity. AI-generated outputs may inadvertently incorporate copyrighted material, exposing businesses to infringement risks. Addressing this requires not just legal safeguards, but also internal governance, clear policies on how AI tools are used and integrated into workflows.
Startups, Regulation, and the Need for Balance
India’s startup ecosystem is vibrant, but it operates under intense pressure, driven by funding expectations, rapid scaling, and the need to prove viability.
In such an environment, governance and compliance can sometimes take a backseat.
Deepthi highlights the need for a more nuanced regulatory approach, one that recognizes the unique challenges faced by startups. Applying the same compliance standards to both startups and established enterprises may not always be equitable.
She advocates for reforms such as audit exemptions in early stages, risk-based compliance thresholds, and greater use of technology to simplify regulatory processes.
At the same time, she is clear that flexibility should not come at the cost of governance. Issues like misuse of funds, related-party transactions, and regulatory violations can damage not just individual companies but the credibility of the entire ecosystem.
Striking the right balance is essential.
The Systemic Challenge: Justice Delayed
Beyond corporate law, Deepthi points to a deeper systemic issue: the burden on India’s legal system.
With over 5.5 crore pending cases and significant delays in dispute resolution, enforcement of legal rights remains a challenge. While mechanisms like arbitration were designed to ease this burden, they too face delays due to judicial intervention.
However, she sees hope in technology.
From virtual courts to AI-driven tools for case management and legal research, the system is slowly evolving. The introduction of the Mediation Act, 2023, which recognizes online mediation, is another step toward faster and more efficient dispute resolution.
For her, embracing technology is not optional; it is essential.
Data Privacy: The Next Big Shift
As India moves toward implementing the Digital Personal Data Protection Act, businesses are entering a new era of accountability.
The law places consent at the center of data processing, requiring organizations to rethink how they collect, use, and manage personal data. For many businesses, especially those without prior exposure to global frameworks like GDPR, this represents a significant shift.
Compliance is not just about legal understanding; it involves operational changes, infrastructure investments, and cultural adaptation.
For startups, the challenge is even greater. High compliance costs and steep penalties can pose serious risks, making it critical to adopt a thoughtful and phased approach.
The Rise of AI and the Question of Trust
One of the most intriguing challenges Deepthi highlights is the growing reliance on AI in legal services.
Clients are increasingly turning to AI tools for drafting contracts, summarizing documents, and even seeking legal advice. While these tools offer speed and efficiency, they also raise important questions.
Unlike lawyers, AI systems cannot be held accountable for incorrect advice. This creates a gap, one that businesses may only recognize after facing financial or reputational consequences.
For legal professionals, this shift is both a challenge and an opportunity. It pushes them to move beyond routine tasks and focus on what truly adds value, insight, judgment, and strategic thinking.
Law in the Grey
Deepthi Rajeev’s journey is a reflection of a larger truth: the future of law lies not in black-and-white answers, but in navigating the grey.
It is about understanding technology, anticipating risks, and crafting solutions that balance innovation with responsibility. It is about moving beyond traditional roles and becoming a partner in building businesses.
Through DRN Legal, she is not just practicing law; she is redefining how it is delivered.
And in a world where change is constant, and certainty is rare, that ability to operate in the grey may just be the most valuable skill of all.
-Interview Conducted By Shivani Solanki
