Stephen Candelmo is a corporate lawyer turned tech founder who has spent nearly thirty years advising emerging companies and building his own ventures. In this episode, he explains how a recession, a machine learning experiment, and a desire for fairness inspired him to create Paralex, a legal platform that delivers fixed-fee, AI-powered legal services for small businesses and startups. He also shares why he believes the legal profession is on the edge of a major transformation.
Corporate lawyer and founder Stephen Candelmo explains how AI, entrepreneurship, and transparency can change the way lawyers work and the way clients access legal help.
Stephen Candelmo grew up in an immigrant working-class family in Pennsylvania. His father, who completed college later in life, consistently encouraged education for Stephen and his brothers, and planted the idea that law school could open many doors. Although no one in his immediate family practiced law, Stephen was drawn to the structured thinking and range of opportunities that a legal education offered. After earning his undergraduate degree, he attended the University of Akron School of Law, followed by additional study in Washington, DC.
“You go to law school, it is going to teach you how to think. You can do so many things with that. They can never take that away from you," shares Stephen Candelmo on You Are A Lawyer.
His early career took shape at a national law firm where he handled corporate work ranging from formations to public market transactions. Although he enjoyed the diversity of his practice, he was also fascinated by business and technology. That curiosity eventually pushed him beyond traditional legal paths and into entrepreneurial ventures, each one laying the groundwork for the company he would later build.
Stephen’s choice to attend law school was influenced by two main factors: his father’s advice about the versatility of a law degree and his own early interest in business. His father believed law school would give him a professional foundation strong enough to pursue almost any path, whether in government, business, or private practice. Stephen also discovered he enjoyed negotiation, financial structure, and helping people reach fair outcomes, which made corporate law a natural fit.
“I always had an interest in business. I liked bringing people together and getting to a fair situation, while advocating for my clients when necessary," explains Stephen Candelmo on Episode 222 of You Are a Lawyer.
Although he did not initially see himself as a courtroom lawyer, he embraced the broader possibilities of a legal career. Law school gave him a toolkit for solving problems, improving systems, and navigating complex decisions, all of which later played a significant role in his entrepreneurship journey.
Stephen’s career is a testament to the flexibility of a legal education. He practiced at a national firm, built a solo practice, and served as a trusted advisor to emerging companies. During the 2009 recession, he launched his first tech company, applying machine learning and sentiment analytics to brand monitoring. That experience taught him how to merge business, law, and innovation.
“Life is uncertain and things will change. The flexibility to go left or right based on the skills you developed as a lawyer will never leave you," shares Stephen Candelmo on Episode 222 of You Are a Lawyer.
He later created Paralex to apply AI to legal work in a way that increases efficiency and reduces cost for founders and small businesses. His law degree did not just provide technical ability. It gave him the confidence to build companies, experiment with technology, and reimagine legal service delivery.
Stephen’s entrepreneurial path began long before Paralex. While still practicing corporate law, he launched a machine learning startup focused on sentiment analytics. The company served well-known customers and gave him a deeper understanding of product design, customer behavior, and the commercial side of technology. Years later, when large language models became available, he immediately began prototyping legal use cases instead of simply experimenting for fun.
“Once you start innovating, you are always on the lookout for the next thing. It becomes a shift in mindset,” Stephen Candelmo expresses in Episode 222 of You Are a Lawyer.
Paralex is the culmination of decades of corporate experience, business curiosity, and belief in legal accessibility. His side ventures were never hobbies. They were stepping stones that helped him create a platform where AI handles routine legal tasks while lawyers provide oversight, judgment, and accountability. For Stephen, entrepreneurship is not separate from being a lawyer. It is an extension of what lawyers can do when they combine their training with creativity.
Stephen is not licensed to practice law.
This episode is produced by Skip The Boring Stuff, a podcast strategy company for business owners and creatives.
