Andrew Lieb, MPH, Esq.

THE STORY BEHIND MY PRACTICE

How I Became a Complex Litigator

Entrepreneurship Before Law

Long before I became a lawyer, I created the exact kind of legal problems I would spend my career litigating.

In high school, I started a tutoring service that grew to 12 independent contractors. Looking back, it's funny to think that I certainly lacked proper independent contractor agreements, the money, or the know-how to build a legal structure for what would happen if the company became wildly successful. I was a kid trying to find customers, manage people, make money, and grow a business.

But that experience taught me something I would spend much of my career seeing again and again. Entrepreneurs have tunnel vision in building for success. Yet, they rarely build the requisite infrastructure necessary to insulate themselves from the multitude of lawsuits they will face as that success manifests. The possibility that litigation is part of every successful business remains a vague concept, pushed aside until the "partners" are fighting tooth and nail over the highly valuable company that was never set up correctly in the first place.

I went to Indiana University and studied at the Kelley School of Business. Entrepreneurship followed me there too. I had a side business renting apartments to college students and learned a great deal about real estate. I stayed at Indiana for my master’s in public health, which taught me to think about statutes, regulations, incentives, changing societal norms, and human behavior.

Learning Law Through Litigation

When it came time for law school, my father had a practical plan for me (since before I was born). He wanted me back on Long Island, going to law school while working in his general practice. So I went to Hofstra University School of Law and worked throughout law school.

That decision shaped me as an attorney. I was studying legal doctrine while spending my working hours seeing how facts, clients, documents, negotiations, and litigation actually came together. My father had a true general practice, so there was no narrow lane. I was exposed to real estate, estates, matrimonial matters, business transactions, and litigation. By the time I graduated, I had already accompanied attorneys through trials and had seen litigation unfold beyond the caselaw I was studying at law school.

After I was admitted to practice as an attorney, I continued handling a broad caseload. I drafted agreements and handled real estate, estates, probate, and business matters and I also litigated disputes involving property, businesses, and their owners.

That combination became foundational to how I think. I learned how attorneys try to document relationships on the front end. Then, as a litigator, I learned what happens when those documents leave important questions unanswered, answer those questions with only vague terminology, do not reflect what the parties actually did, or simply do not exist. Simply, the contract often does not reflect what the parties actually did, or it simply does not exist.

And the more I litigated, the more I knew that was where I belonged.

I liked difficult facts and nuanced law. I liked cases where the documents did not neatly answer the question and where two intelligent people could look at the same history and tell completely different stories. Most of all, I liked finding the thread that made a complicated dispute understandable. It felt like building a puzzle with thousands of pieces.

Building a Complex Litigation Practice

I wanted to build my career around that kind of work, so I left my father’s general practice and founded Lieb at Law.

Around the same time, I founded a licensed real estate school and began teaching compliance to real estate brokers and salespersons. I eventually built an online, on demand school that educated more than 10,000 students in New York.

Unexpectedly, the school became an engine for the law firm. General counsels of major brokerage companies began retaining us, and the litigation became increasingly complex. This started with a strong foundation in real estate and then expanded into commercial disputes, employment and independent contractor matters, ownership and compensation fights, regulatory proceedings, and cases where several areas of law collided.

Over time, Lieb at Law evolved into a litigation boutique. We began handling complex disputes in state and federal courts, before various arbitration providers, administrative agencies, and other forums. Our practice expanded beyond Long Island to the rest of New York, and into New Jersey, Connecticut, and Colorado. Our attorneys have appeared pro hac vice in substantial matters around the country. Larger firms began referring us matters when they were conflicted out from representation and, eventually because they found us adept at handling technically difficult litigation that required an infrastructure ready to litigate across traditional practice areas.

Those became the cases I loved.

A business dispute might turn into a corporate governance matter and also involve employment law claims. An ownership fight might require understanding real estate, financing, compensation, trusts and estates, or regulatory law. An employee might claim promised equity. An independent contractor might argue that the relationship was completely different from what the documents called it. The field could be regulated by its own body of law that changes the respective rights of the parties.

Sometimes what appeared to be a contract case required reconstructing years of conduct among founders, employees, investors, family members, and other stakeholders.

Making Complexity Understandable

At the same time, another part of my career was developing that I did not initially realize was connected.

I had been publishing in legal journals and teaching CLEs to attorneys when reporters began calling me. When a new law, regulation, or court decision came out, outlets including The New York Times and Business Insider, as well as local and national news stations, would reach out because they needed someone to interpret what had happened and explain what it actually meant.

That eventually led to a period where I worked extensively as a legal analyst, making hundreds of television appearances.

I discovered I had a talent for taking complicated law and complicated facts and stripping them to the basics to make them understandable.

A reporter did not just need someone to recite a statute. The audience needed to know what changed, why it mattered to them, and what would happen next on the topic.

The more I did it, the more I understood that simplifying something is not the same as making it simplistic. You have to understand a subject deeply enough to know what matters and what does not.

I eventually realized that was also a large part of what I loved about complex litigation.

A case can contain tens of thousands of pages of records, years of emails and texts, multiple witnesses, conflicting documents, competing narratives, and several bodies of law. The job is not to repeat all of it. The job is to find the facts that matter, connect them to the law, and build a theory of the case that makes the complicated understandable.

Technology has increasingly helped us do that. When AI became commercially useful for legal work, we began incorporating it into appropriate litigation workflows to analyze large records, reconstruct timelines, compare documents and testimony, identify inconsistencies, and find connections across complicated evidence.

The lawyer still has to verify the work, understand the law, exercise judgment, develop the strategy, and advocate. But the ability to interrogate information at scale has changed what a litigation boutique can do with an enormous factual record.

Then entrepreneurship came back into my career from a completely different perspective when I was approached to become chairman of a tech startup.

By then, I had litigated enough business disputes that I entered the boardroom intensely focused on ownership and governance. Who owns what? Who has authority to make which decisions? What rights do investors have? What changes when new capital comes in? What happens as the company grows and everyone’s incentives begin to change?

I experienced raising capital, state securities laws and SEC compliance, investor and ownership interests, governance, and how each stage of growth can change the relationships among the people involved. Eventually, I had an opportunity to sell my interest in the company and decided the timing was right.

That experience gave me another perspective on issues I had spent years litigating. It also gave me a greater appreciation for what a strategic board and good governance can contribute to a growing company.

Finding the Pattern

By then, I had started seeing the same fundamental problem from almost every direction.

I had been the entrepreneur whose legal documents were never designed to anticipate every issue that could arise if the business became significantly more valuable. I had worked in a general practice while studying law. I had handled transactional matters and then litigated what happened when relationships broke down. I had built a complex litigation practice. I had taught attorneys and spent years translating complicated law for the public. I had experienced ownership, capital raising, and governance from inside the boardroom. And I had watched technology change both how people create legal relationships and how litigators can reconstruct them.

Eventually, I started noticing that some of our most complicated cases looked completely different when they came through the door, but underneath, they were remarkably similar.

One case might be called a commercial dispute. Another an employment case. Another a real estate ownership dispute, partnership fight, derivative action, or estate controversy.

But we were often solving the same fundamental problem.

The relationship had become valuable faster than the legal structure around it had matured.

Someone contributed money. Someone else contributed the work. An early employee was promised equity. An independent contractor believed there was a path to ownership. Investors arrived at different stages. Family members contributed money or property. People had different ideas about who owned what and who was entitled to what.

They shook hands. They texted. They emailed. They downloaded templates. They formed LLCs but never finished the operating agreements. Now they can ask AI to generate documents that look extraordinarily formal without necessarily understanding the legal consequences of each provision, much less every term.

Everyone assumes they will clean it up later.

Then later arrives after there is real value at stake.

An owner wants out. An investor wants control. An employee claims equity or compensation. A contractor disputes the nature of the relationship. A founder dies. Family members inherit interests. Property appreciates. New investors arrive. Greed sets in. Five people can have five different versions of what everyone agreed to.

By the time the dispute reaches the litigator, there may be no single document that provides the answer.

There may be contracts, texts, emails, employment records, financial records, corporate filings, testimony, and years of conduct pointing in different directions.

You have to reconstruct the relationship.

Who contributed what? Who owns what? Who controls what? Was someone an employee, independent contractor, partner, member, or investor? What compensation, equity, or financial rights were actually created? What did the parties do? What can the evidence prove?

And those questions rarely belong to only one field of law.

An estate attorney may be dealing with several heirs after a business owner dies, only to discover that determining what passes through the estate first requires resolving whether the decedent actually owned the business interest everyone assumed was his. That may depend on an operating agreement, the deed, a missing filing from years earlier, capital contributions, corporate records, or the parties’ conduct.

A real estate dispute may appear to be about selling or partitioning a valuable property until the threshold question becomes whether the property is owned individually, through an LLC, or as part of a partnership business venture, and who actually has the legal and economic rights to control it.

An employment dispute may begin with unpaid compensation and evolve into a fight over whether the employee was promised equity and if that equity was stripped while they were harassed on the job.

A commercial litigator may be asked to enforce a contract only to discover that the outcome depends on entity formation, governance, employment law, real estate law, trusts and estates, securities issues, or years of conduct that do not match the documents.

The practice areas are distinct. The dispute is not.

That was the pattern I kept seeing. That was the puzzle.

The hardest cases were often difficult precisely because no single field of law supplied the whole answer. The parties’ rights existed at the intersection of multiple bodies of law, and the litigator had to understand how those bodies of law interacted before determining what the evidence actually established.

Eventually, I realized I had not spent my career practicing a collection of unrelated areas of law. I had spent it learning how to litigate disputes that sit at the intersection of them, where ownership, control, compensation, governance, property, inheritance, and contractual rights can all depend on one another.

That was the insight that ultimately became Napkin Litigation™.

Napkin Litigation is a field of law for disputes where the deal, relationship, or asset is real and valuable, but the documentation, governance, employment structure, or other legal protections did not keep pace. The litigator has to reconstruct what actually happened, establish the parties’ legal and economic rights, build leverage, and protect the value at stake.

In many ways, the skill that has followed me throughout my career is the same one: take something incredibly complicated, find what matters, make it understandable, and use it to build a litigation strategy.

Napkin Litigation grew out of the cases we were already litigating at Lieb at Law. It was not something we created in the abstract and then went looking for cases to fit within it. We recognized the field because our litigators kept confronting these disputes and seeing the same patterns across traditional practice areas.

Today, that work is continuing in two directions.

Our team at Lieb at Law continues to litigate these complex disputes, while we are also developing the Napkin Litigation methodology and training attorneys nationally through CLE programs on how to recognize, analyze, and litigate them.

That combination matters to me. I do not want Napkin Litigation to become theory alone; an academic concept removed from the disputes that created it. The methodology should continue to be tested and refined through actual litigation, new decisions, new technologies, and the increasingly complicated ways people create businesses, structure relationships, and accumulate value.

My career started as a kid building a business without thinking very much about the legal structure around it.

Years later, I became the litigator hired when businesses and relationships, built much like my high school business, became valuable enough to fight over.

It took me years to realize those experiences were interconnected.

Now, alongside a dynamic team of complex litigators at Lieb at Law, I get to fight those disputes, develop the methodology for approaching them, and teach other attorneys nationally what we are learning along the way.

That is where my career has taken me.

And I think we are just getting started.