“Law wasn’t a detour, it was a logical conclusion of my evolution from being just a writer to being one who writes to ensure that justice is available to everyone in need of it.” – Siddharth Chandrashekhar, Sr. Panel Counsel CBIC/DRI & Standing Counsel CBDT, Bombay High Court.

This interview has been published by Anshi Mudgal and The SuperLawyer Team

What inspired you to pursue a career in law?  Was there a particular moment, influence, or personal experience that drew you to the legal profession? 

Since the time I learned to read and write, I have been a voracious reader. This passion led me to a deep interest in literature, history & political science. Everything I could lay my hands on, from William Shakespeare to Edgar Allen Poe to George Orwell and William Wordsworth to Arthur Conan Doyle, Oscar Wilde & of course Haruki Murakami. I was fascinated by how stories shape society and I was certain that I would either end up as a journalist chasing and breaking news stories or a writer churning out books and articles.

My family of lawyers, journalists and politicians encouraged me to develop my writing skills by reading.  Contrary to popular belief, being a second generation lawyer is not always easy. In fact, like in my case, the bar was already set high by the rest of my family, and I knew that nothing less than excellence would be acceptable should I decide to join the legal practice and forge a career in law. However, my first choice was to be a journalist. 

But one day during the Diwali/Winter break in my final year of studying for my Bachelor’s degree in Arts as I had made no plans to spend time in recreation with my friends, I decided to attend a cross-examination being conducted by my Advocate aunt when I watched her meticulously extract the truth with surgical precision from a witness on the stand with. The next day I requested my father, who had a flourishing legal practice in civil disputes and trial courts, if I could intern with him for a week. He agreed on the condition that I had to work even harder and put in more hours that week than the rest of the interns and not look at the clock. The first day I sat with him while he painstakingly drafted and re-draft a legal notice meticulously with the skill of what I could barely fathom. We must have spent close to 16 hours that first day, and much to my surprise, I was back again the next day where we spent another 16 hours, and I kept my word, I was the first to arrive and the last to leave. At the end of that week, I made up my mind to pursue a career in law.

 Thus, Law wasn’t a detour, it was a logical conclusion of my evolution from being just a writer to being one who writes to ensure that justice is available to everyone in need of it. 

What motivated you to pursue your master of laws degree (LL.M.) from Queen Mary University of London?  What aspects of the program & institution aligned with your academic and professional goals? What are your key takeaways & experiences from your time there ? 

If the degree of Bachelor of Laws was the foundation for my legal practice , my Masters in Law at Queen Mary, University of London was what built the edifice  from which I could have a world view of international legal trends at and the ever widening scope that law provides to ensure a more equitable world. Out there I wasn’t analysing just the law in theory, but society and the way we function in relation to the law which gave me tools to further my learning. 

Most of India’s statutes have either been drafted while we were a colony of the British or are based on laws in the U.K. In that sense Queen Mary offered me a historical mirror coupled with a modern lens, which made it ideal for my practice in Corporate & Commercial law. I chose Queen Mary because its LL.M. was famous for being both rigorous in theory and incredibly practical. It felt less like a classroom and more akin to partaking in real world legal scenarios. Three factors converged to create the perfect storm: In fact, prior to my LL.M. degree I had already been advising startups on Transactions, Litigation Avoidance advisory and Pre-Litigation when I realized that understanding international commercial law wasn’t optional anymore, it was the only means of raising India to the highest international standards.  Second, London’s position as a global financial hub meant access to case studies that textbooks simply cannot replicate. Third, QMUL’s University’s faculty included practitioners who wrote the rulebooks on disputes and dispute avoidance.

My Master’s Degree in law laid an emphasis on comparative legal systems which proved invaluable to me now in my legal practice. Part of socialising and networking would regularly involve heated debates with faculty and peers which were our own version of the Oxford Union debates where we dissected existential legal conundrums faced in transactional agreements under Indian, English, American (Delaware), and Singapore laws. These were followed by a round of Hors d’oeuvres and drinks for which the lawyers who had failed to win the crowd would have to pay for it. The program’s real value wasn’t in the lecture halls but in the conversations that followed afterward. Late-night debates at the pub about whether certain aspects of media law really needed new legal frameworks, weekend trips with peers, faculty and chance encounters with renowned QCs & KCs. 

These sessions taught me that Law isn’t just about a set of rules, it’s the art of predicting human behavior within social constraints. That became my mantra. Even my dissertation became the foundation for later advising several startups on their transactional and regulatory strategies. My London experience taught me that legal advice without commercial context is akin holding G.P.S. hardware with no connection to satellites and software, technically sophisticated, but practically useless. London offered something Mumbai could not at that time, proximity to the birthplace of commercial law and traditions that govern global transactions even today. London taught me two things: how to use the law with surgical precision and how to survive in a multi-cultural metro much akin to my own home city of Mumbai, with the only difference being that it wasn’t ‘Home’.  

Queen Mary wasn’t just a campus; it was a court room without borders. I chose it for its emphasis on comparative commercial laws and of course, being in London, the commercial capital of the world was the icing on the cake. Every lecture was an eye opener to the world’s legal machinery and watching it in motion. We didn’t just study corporate and commercial law but we debated it with both present and future public policy influencers. It provided me with the opportunity to interact with vanguards and scholars of law and economic policy in our classrooms and campus. Of course, having such as alumni consists of stalwarts including India’s former RBI Governor Mr. Urjit Patel, Economist Pranoy Roy & Davidson Nicol, the former Under Secretary General of the United Nations makes it stand out even more.  

Legal expertise without cultural fluency is like using complicated words with no proper context in an unrecognisable language. The LL.M. taught me to be multi-lingual in legal traditions essential for any lawyer serious about Start-up advisory in our globalized world.  

In the early stages of your legal career, what experiences or matters significantly enhanced your understanding of the Law? Are there any pivotal moments that helped shape your professional trajectory? 

If law school is your boot camp, then your initial few years of practice are akin to active combat duty. My father who was my mentor when I joined the profession has a saying: “Every mistake you make costs someone else money, time, or opportunity, so be extremely alert you may make new mistakes, but never repeat the old ones which you must use as a means of from your old ones which you must use as a means of enhancing your knowledge.”. Those words transformed how I approach every Start-up advisory engagement. 

Every lawyer has that one case or a few early on in their career that serve as their trial by fire. Mine involved a tech Start-up whose founders had structured their equity like a Rom-Com love triangle, complicated, dramatic & destined for disaster. As we worked towards reconstituting the documentation, one thing was clear to me, ‘Startup Law’ (as people have labelled it) isn’t about preventing problems, it’s about creating efficient solutions for smart people who often make predictable mistakes. That client taught me three things: First, documentation matters, but context matters more. Second, the best legal advice often sounds like business advice. Third, sometimes the best service you can provide to a client is talking them out of their own cleverness. 

Another pivotal moment came during my first due diligence exercise for a Series A round. Thirty hours into document review, I discovered a licensing agreement that could torpedo the entire deal. The lead investor later told me that I didn’t just save them money, I saved them from becoming a cautionary tale. My (Late) Grand-mother, who was a highly respected and loved State Legislator once told me: Good lawyers know the law; great lawyers understand the story behind the enactment of that law. That’s when I realized that due diligence isn’t treasure hunting; it’s about defusing land mines. These experiences of multiple successful people shaped my philosophy: Be the lawyer who prevents a crisis, not one who profits from it. 

One of my first major transactions involved a then small scale e-commerce startup with revenue in different jurisdictions and compliance documentation in none of them. It was like being asked to perform surgery with a plastic knife. We spent several weeks creating the legal infrastructure for them which in fact should have existed from day one. One of its founders later said, ‘We thought that legal documentation was trivial until we realized it was life support.’  

You advise & litigate for several major government bodies as a Senior Panel Counsel for the Directorate of Revenue Intelligence (DRI)/GST Intelligence & Central Board of Indirect Taxes (CBIC) as well as Standing Counsel for the Central Board of Direct Taxes (CBDT), & Maharashtra Housing & Area Development Board (MHADA)  AND  being a legal advisor to several Start-Ups in the tech & media space on the other how has working across such diverse institutions influenced your legal approach?  What have been some of the most challenging matters among them? 

My experiences with government agencies and statutory bodies taught me to navigate bureaucracy not as an obstacle, but as a playing field where real business gets done. This perspective proves invaluable when guiding startups through regulatory approval processes. Of course, I have been blessed and privileged to have had the opportunity to work with some of the most intelligent, upright & hard-working officers right from the grass-roots level Inspectors & Superintendents to Legal Advisors/Officers from right at the top up to (Chief/Joint/Deputy)  Commissioners, A.D.G., Deputy & Joint Directors, so I have to give them credit where it’s due. If I have to sit and name them all that in itself would be a fairly long list.  

 Diversity proves invaluable for Start-up advisory work. When advising media houses or fintech companies, It’s not just about understanding MCA, RBI, SEBI, SWA regulations, It’s about deciphering the Regulatory and counter party mindset, the concerns that keep regulators awake at night, and how policy gets translated into practice. 

That lesson now translates directly into how I work with startups and media houses. I cannot count the number of times boot strapped founders have met me and said “We don’t need the paperwork, it’s fine, we trust each other” only to reappear a few  months later realising that when disputes arise trust flies out of the window. My early career showed me that cross-checking every consent form, every signature, every assumption can mean the difference between smooth sailing and sinking fast. 

Despite my LL.M. specialisation I never restricted myself to one particular area of practice, which is why I now am able to decipher matters ranging from Income Tax disputes, Customs act & GST related Writs, Appeals, Bail & Anticipatory Bail dealing with Tax Evasion, NDPS cases, Housing disputes & other laws. Working across government bodies is like playing five-dimensional chess with tax intelligence, urban planning, housing rights, anti-evasion laws being the pieces on the chess board. Each brief requires switching mental gear and watching details with varied legal lenses. I’ve argued tax evasion by breakfast and housing and society related issues in the second half. 

Working with multiple statutory bodies is like being a legal anthropologist and a linguist, each institution has its own culture, priorities and rules, both written and unwritten. My empanelments read like a tour of some of India’s most fascinating legal statutes including The Black Money (Undisclosed Foreign Income & Assets) and Imposition of Tax Act, Finance Act & Income Tax Act under the CBDT, the Goods & Services Act, Customs Act & Narcotics & Psychotropic Substances (NDPS) Act under the CBIC & DRI and the Maharashtra Housing & Area Development Act, to name just a few. 

Each case has been fascinating and just like fingerprints no two cases are alike but one of my most fascinating as well as challenging one has been a Writ Petition filed by one of the world’s largest manufacturers of automobiles having it’s parent company based in Germany who had sought to quash & set aside a $1.4 billion Show Cause Notice issued by the Office of the Commissioner of Customs based on investigations by the Directorate of Revenue Intelligence for wilful tax evasion  misclassifying imported car parts to avail lower import duties. In that case, I was led by the Learned Additional Solicitor General (ASG) of the Government of India who used to regularly fly down from New Delhi to argue the case. It was like solving a Rubik’s cube while being blindfolded where every move in one dimension affects others. That case taught me that regulatory strategy isn’t merely about simple compliance or the lack thereof with statutory provisions which may appear uncomplicated but a complex choreographed play involving multiple issues which ought to be viewed from multiple angles to get a holistic picture and arrive at what requires to be followed in practice. 

Another case involved the challenge to an incorrect and manipulated technical opinion given by a multi-national consultancy firm to a multi-national South Korea based conglomerate who imported electronic equipment worth billions of dollars under a wrong entry based on the aforesaid technical opinion.  

Yet another case involved a challenge to a pivotal aspect of tax administration which involved the transfer of a group of cases from one Assessing Officer (AO) to another and was crucial in ensuring the smooth functioning between two different state jurisdictions of the tax administration where the Assessee raised objections to the change in jurisdiction. 

The diversity proves invaluable for startup advisory work. When advising Start-ups and individual entrepreneurs, I don’t just have to understand and simplify regulations I have to understand the regulatory mindset, the concerns that keep regulators awake at night, and understand how policy has to get translated into practice. 

My government litigation experience taught me to navigate bureaucracy not as an obstacle, but as a playing field where real business gets done. This perspective proves invaluable when guiding Start-ups through regulatory approval processes. It has helped me to represent my private clients in their attempt to bridge the gap between legal theory and public policy reality. 

Each role brought with it unique challenges, serving on regulatory panels involves balancing innovation with protection, investigating financial irregularities requires detective skills which they don’t teach you in law school, and where policy advisory work demands thinking beyond individual cases to systemic implications. 

Yet another challenging matter pertained to a multi-agency investigation into a scandal involving small individual investors on the one hand and a group of companies, whose interests ranged from real estate development to cattle rearing to broadcasting services. Over three years, multiple stakeholders, and countless sleepless nights later, we crafted a resolution that protected investors while preserving innovation incentives. The experience taught me that public service isn’t about serving the law, it’s about serving justice through the law. 

The experience of working with government bodies and statutory bodies transformed my startup advisory practice. I don’t just help companies comply with regulations; I help them understand the ‘why’ behind the rules. When founders grasp regulatory intent, they can work smoothly within set boundaries rather than riding rough shod over the set perimeters. These roles have made me lawyer, policy analyst & virtual entrepreneur. When advising CBIC on procedural lapses or individual entrepreneur clients, I often have to translate complex regulations into implementable steps. That cross-sectoral experience honed both my legal acumen and empathy to various causes. 

You’ve actively participated in pro bono matters & causes varying from human rights to animal welfare, including filing public interest issues before the hon’ble Bombay High Court.   What drives you to take up such socially significant and often challenging cases?   In your view, what role should pro bono work play in a lawyer’s practice?   You’re also a legal advisor to Sanctuary Foundation and Fur-rida’s Animal and Rehabilitation Trust, NGOs dedicated to Animal Welfare & rehabilitation in Mumbai,  how do you balance both out? 

Pro bono work, for me, began as a calling of my conscience. As a lawyer when you only litigate on behalf of  those who can afford it, you are not helping the cause of justice but only helping those who are already privileged. Pro bono work always reminds me why I became a lawyer: not to rake in the money, but to actively work towards changing our world for the better, using the opportunity to advocate for a better, fairer and more equitable society. Billed clients feed the body. Pro bono work feeds the soul. 

But here, before I even begin to think of taking any personal credit I must mention that it was the elders in my family for instilling whose values instilled in me makes me give back to society. My Late grandfather, an industrialist paved the way by social and charitable work. My Late grandmother was a Mumbai City Legislator and later Maharashtra State Legislator from the 1990s to the early 2000s. My Late uncle, also a businessman, sacrificed his business interests to champion the causes of the common man and was well known as a vociferous advocate of causes who many felt were lost causes. Just the three of them were responsible for providing basic sanitation and piped water connections to lakhs of residents of informal settlements in underserved parts of (South) Mumbai and also later went on to build study centres and gymnasiums for the poorer class of citizens who could not afford these “luxuries” throughout (South) Mumbai.  

I grew up watching my father put in the same dedication and hard work into his pro bono clients that he would into his millionaire clients and once (while I was very young) I asked him why he did this, he simply said, If I don’t, then who will? … and that rational question just stuck with me. My mother gave up a very promising career as a journalist to teach journalism, creative writing and conduct writing boot camps. My brother, now a high-profile Surgeon still spends days working pro bono and organising medical camps in rural Maharashtra where there is little to no expert medical facilities. Another uncle is a senior journalist who has covered some of the most ground breaking issues of the time, not stories about luxury but the ones that no one else dared to cover because he felt that someone had to take up such matters. Another aunt gave up her job as a Banker to teach children. 

When the Covid-19 pandemic hit India people had to take recourse to the Covid vaccine as it appeared to be the only defence against it. However, some unscrupulous elements took advantage of the rush for the vaccine and started administering mere saline water and passing it off as the Covid Vaccine. When my aunt, and I heard of it we couldn’t ignore it. The idea that thousands of people were tricked into believing that they were being given the vaccine when in reality they were not, shook both of us. Our PIL on this issue wasn’t just about a legal remedy, it was about restoring public faith in the ability of the  law in dealing with such unscrupulous elements. 

What continues to drive me is the belief that law must serve those who can least afford it. If startups look to me for guidance on shareholder rights, ordinary citizens need me for something far more basic: the right to life and health. In my view, pro bono isn’t charity, it’s oxygen for the soul. It reminds us why we became lawyers in the first place. As William Scott Downey had aptly put it, Law Without Justice is a Wound Without a Cure. 

 Pro bono litigation is not mere work without purpose in monetary terms, it’s about priceless work for those who cannot afford to pay to get good legal representation. I believe every lawyer who has crossed 10 or more years of practice must dedicate a part of their practice to Pro Bono Litigation. Otherwise, we risk becoming mere paper pushers and money making soulless machines instead of custodians of real justice. 

Once I found myself in the thick of a case involving a teenage boy who died after being detained and allegedly tortured by the police whilst in their custody. The boy, barely 17 years old from Mumbai’s Dharavi slum district, was accused of stealing a mobile phone. After being released from “routine police detention” in July 2018, he complained to his parents and siblings of his torture by the police while in their custody. Soon after his release, he developed a fever, and his condition deteriorated rapidly, and he tragically passed away within a week. The post-mortem report mentioned pneumonia as the cause of his death. To everyone but his family, the case was as good as closed. The family’s grief was not just raw, it was distrustful of the very system that swore to protect them and it was absolutely justified in refusing to take their child’s body for his last rites for nearly two years until the High Court ordered a second post-mortem. For those two years, the body lay unclaimed in a morgue, almost frozen in time. But the law did not forget him and nor did I.  

I wasn’t new to litigation then, but here I learned something every statute book misses: law isn’t just about sections and precedents; it’s about instilling trust in those for whom laws are enacted. The Hon’ble High Court’s order was a pivotal moment it showed me about the compassion and kindness of judges and it showed me that you don’t need to have the loudest voice to tilt the scales of justice in favour of the helpless and restore faith in the judiciary. It also sharpened my skills in due diligence because when you’re digging through contradictory medical reports and hospital records, you learn how to scrutinize details like an auditor hunting for hidden liabilities.  

Taking on that case was not about earning any fees as it was completely pro bono, it was the weight of my conscience which guided me to do so. That case became my personal reminder that law is not always swift, but it is relentless. Sometimes you carry files that weigh more than law books they weigh with grief, suspicion, and silence. 

Another matter that shaped my formative years was one that involved a medical negligence case where a woman contracted Hepatitis C after a hysterectomy at a famous South Bombay hospital. A team of surgeons and doctors, one operating theatre, and a chain of negligence right from the top, it was a puzzle of medical protocol and accountability. For a young lawyer, it was baptism by fire. I spent nights reading medical manuals, learning how a surgery should be conducted, and finding out with what went wrong. What it taught me is that the devil truly hides in the documentation. 

Pro bono cases also tend to surprise you and throw you into the deep end, no fees, minimal support, high legal stakes for those involved. But they also teach you to think creatively and advocate fiercely. They’re a bootcamp for both skill and conscience.  Pro bono work teaches you humility: you are not always the smartest person in the room, sometimes you are the only person standing between injustice and justice. 

Animal welfare law in India is like a crossword puzzle with half its clues missing. As advisor to Stranctuary Foundation and Fur-rida’s Animal Rehabilitation Trust, I have actively helped them get set up as well as look into internal policy and legal fine print. I’ve worked on matters involving animal cruelty, harassment from societies against members from using elevators or accessing common areas with their pets. These cases taught me that education is as vital as litigation. Sometimes, the law needs a lawyer often it needs an earnest storyteller. “Until one has loved an animal, a part of one’s soul remains unawakened.” – Anatole France 

Pro bono work should be mandatory in every lawyer’s practice, not as a penance for making money, but as a training for making better decisions. Every PIL or Pro Bono Writ I advise on makes me a sharper commercial lawyer because it reminds me that law exists to serve, not the other way around. Plus, there’s practical value: Pro bono cases often involve cutting-edge legal questions that commercial clients pay premium rates to explore. It’s continuing education coupled with social service. My pro bono work began with the simple realization of the advice of my (Late) grandmother who told me: Corporate law pays your bills, but public service will reward you with a clear conscience and a good night’s sleep. When you spend your days crafting shareholder agreements and due diligence reports, you can lose sight of law’s fundamental purpose of protecting the vulnerable and ensuring fairness. Pro bono work keeps me honest. 

Every time I review a startup’s employment policies, I remember the domestic workers whose rights I’ve advocated for. Every time I structure a complex transaction, I’m informed by cases where transparency could have prevented injustice. It’s enlightened self-interest: Better lawyers emerge from engaging with law’s moral dimensions, not just its commercial applications. 

And oddly, these cases have made me sharper in my commercial practice. Start-ups come to me with messy equity structures, hidden liabilities, and co-founder disputes. I approach those files with the same rigor I did in the case of the boy’s family who allegedly died as a result  of custodial interrogation, digging until the truth emerges from a metaphorical mountain of dirt and stones which seek to hide it. Pro bono makes your professional muscle stronger, because when you stand against the State or against a famous hospital with unlimited resources and a legal team the size of a small army for free, a mere shareholder squabble doesn’t scare you. 

Why take up pro bono cases? Because the power of the law is meaningless unless it reaches those who most need it. The directing of a second post-mortem after a teen’s death or holding doctors accountable for medical negligence are milestones for society and for any lawyer involved in pursuing such cases. 

Looking ahead, what is your vision for the future of your legal practice? How do you see your personal journey evolving within the legal field? In a profession that is both demanding and dynamic, how do you maintain focus, purpose, and mindfulness?

My future vision is to promote people to start building a hybrid practice where commercial matters fuel a strong public interest wing and not just something which has purely commercial motivation. Think of it as the Robin Hood model: charge the rich, fight for the voiceless. 

The future belongs to lawyers who can speak three languages fluently: Law, business, and technology. I’m building a practice that serves as a bridge between these worlds, helping founders navigate not just current regulations but anticipate future ones. 

As for purpose: I want my legacy to be measured not in my tangible assets, but in barriers removed, regulatory hurdles that no longer impede innovation because I found simple solutions, and compliance frameworks that enable rather than constrain entrepreneurial ambition. My goal isn’t to be the most famous lawyer or the richest one, it’s to be the one clients trust with their most important decisions because they know I’ll give them efficient solutions within the parameters of the law and not just some short sighted temporary balm for any problems that they could encounter. 

The legal profession needs fewer disruptors and more steady ships. Staying focused requires principled pragmatism. When faced with ethical dilemmas, I ask not ‘What’s legally permissible?’ but ‘What would I want my family & friends  to be told about me as a lawyer and a human?’ This compass has never steered me wrong. I see myself evolving into policy advisory roles, where law meets legislation. I mentor young lawyers and young law students, and I hope to  use this to build a legal aid network where all of us endeavour to focus just 30% of our time and resources towards pro bono legal aid in india focussing on individual cases and causes ranging from human rights, prevention of  domestic violence and animal welfare cases.  

My five-year vision: Become the first and last go-to legal strategist for Tech & Media Entrepreneurs and Start-ups tackling challenges such as: Intellectual Property Protection, Transfer & Monetization, Data Privacy & Compliance, Fund-raising & Investor relations, Content Liability & Platform Responsibility, Technology Contracts & Partnerships, Regulatory & Policy Navigation and the biggest & most common one being: Dispute Prevention & Legal Crisis Management.  These companies don’t need traditional lawyers; they need legal pioneers who can craft frameworks for technologies that don’t yet have regulatory precedents. Maintaining focus requires what I call ‘productive paranoia’ constantly asking ‘What could go wrong?’ not from anxiety, but from genuine curiosity. Mindfulness comes from remembering that every legal document I draft affects real people’s lives and dreams. 

My endgame? To be feared by crooks, respected to be fair by counter-parties and of course, followed by puppies, especially the ones that have no place to call home. 

Focus and mindfulness? I journal, I used to learn Salsa & Bachata, popular latin american dances, I also took up MMA and found that to be a great stress-buster, I spend time taking care of my dogs as well as feeding a few community dogs. I take breaks from the screen.  “The law is a jealous mistress, but she respects a loyal one.”   

I have one rule which most of my clients are already aware of: if it’s urgent I’ll be drafting and doing research even if it’s 3am or a holiday, but if it doesn’t need urgent redressal I stop working by 9 pm. Balance isn’t a luxury, it’s how I keep the fire burning without burning out. 

Based on your extensive experience across sectors, what advice would you offer to young lawyers just starting out in the profession? Are there any particular resources or habits you would recommend to help them build a strong foundation?

Your law degree is just a learner’s license. The real exam begins in court. Try and read at least one interesting case law a day or at the very least. Argue (respectfully) with your peers. Your opponents and counter-parties are not your enemies. In litigation, your opponent is your adversary, but only inside the courtroom, they are your peers, your colleagues, your juniors and seniors outside the courtroom, treat them all with the same respect once your matter is over that you would want them to treat you with. 

Even if you’re being appointed just for an adjournment, read the entire case, carefully, make sure if given the opportunity by the court, you answer correctly and confidently, most judges asking you about your case are providing you with an opportunity, they know they may lose time with a young lawyer, but they are trying to help you and not put you in a spot. 

Your counter-parties are not your adversaries, you have a common goal, mutual co-operation and trust go a long way here, far longer than brow beating or one-upmanship.  Write even when no one’s reading. Don’t confuse over-confidence with Confidence. But humility is better. Young lawyers often worry about the wrong things. 

Here’s what actually matters: Master the fundamentals before chasing specializations. You can’t advise on complex M&A structures if you don’t understand basic contract principles. It’s like trying to compose symphonies before learning scales. 

Your first five years will feel like everyone’s speaking Latin while you’re struggling with the alphabets, that’s okay, read and re-read. The lawyers who succeed aren’t the smartest ones, they’re the ones who can admit ignorance, ask better questions, and turn feedback into improvement rather than taking it personally. Clients hire lawyers to solve problems, not to demonstrate legal knowledge. Be solution-oriented, not statute-oriented. 

Stop thinking like a student who merely asks for answers and start thinking like a strategist who helps clients navigate ambiguous situations. Law school teaches you what the law says; practice teaches you what the law means. 

In start-up advisory, I’ve learned that founders and investors speak different languages, even when using the same words. ‘Aggressive timeline’ means ‘next week’ to founders and ‘next quarter’ to VCs. A founder once wanted to structure their Series A with several different classes of shares: one for each team member’s ‘unique contribution.’ We simplified to three classes and closed the round in half the time. Then there was the time that Start Up wanted to grant equity to advisors before clarifying their intellectual property ownership. We sorted IP first, advisory agreements second. One recent challenging due diligence involved a company with operations in four countries, three legal entities, and legal documentation that looked like abstract art.  

Good legal advice feels expensive until you need it, then it feels cheap. My approach is preventive medicine for businesses, identifying potential complications before they become complications. Whether it’s crafting founder agreements that anticipate future disputes, structuring employee equity plans that scale with growth, or creating compliance frameworks that evolve with regulation, the goal is always the same: Build legal infrastructure that enables business success rather than constraining it. Benjamin Franklin said, ‘An ounce of prevention is worth a pound of cure.’ In startup law, an hour of careful drafting can prevent months and sometimes years of expensive litigation. Don’t aim to be the smartest/richest lawyer. Aim to be the one your client calls first when they need a solution. 

Four Non-Negotiable Principles: 

1. Understand not just legal implications but business consequences. 
2. Sometimes the best legal advice is telling clients what they don’t want to hear. 
3. Your career will be defined not by the cases you win, but by the problems you prevent and the trust you build. Be the lawyer people call not just when they’re in trouble, but when they want to avoid trouble altogether. 
4. The moment you think you know everything is the moment you become dangerous to yourself, as well as your clients. 

Essential Habits: 

1. Read everything thrice, once for content, once for implications, and once again for good measure.  
2. Make time for one pro bono brief,  at least once a month. 
3. When you aren’t reading, attend court like an obsession: watch, make notes, learn. 
4. Kindness, not money, makes the world go round. Be Kind… Always, especially when you would not benefit. Be kind to those less fortunate than you, how you treat a clerk or a peon is a lot more telling of your character than how you behave in front of a Judge or a Senior Advocate.  Be kind to people, be kind to animals.
5. You don’t have to be the biggest fish in the court-room or the negotiation table, remember piranhas bite more sharply (but remember, above all, Kindness) 

Get in touch with Siddharth Chandrashekhar –