Why This 30-Year-Old Vanderbilt Valedictorian Left Her Big Law Job to Start an AI Company

Long before she ever set foot at Harvard Law, Logan Brown was a child in suburban Kansas, captivated by the courtroom dramas flickering on her family’s television. Brown was transfixed by Law & Order: SVU reruns and Elle Woods’s improbable rise in Legally Blonde. Somewhere between the cross-examinations and the pink-suited triumphs, a switch flipped: Brown decided she was going to be a lawyer.

The next step came with the kind of reckless confidence only a middle schooler could muster. She typed up a resume and cover letter and marched straight into the local district attorney’s office to ask for a job. She was twelve years old.

Most adults would’ve smiled and sent her home, but a secretary named Dolores saw something earnest in her. Dolores made Brown her unofficial intern, letting her file paperwork, run coffee and linger in courtrooms. That summer, and many more to follow, Brown trailed lawyers, judges and staff through the courthouse corridors, learning how the law actually worked. To Brown, the experience felt like a glimpse inside the career she was meant to build.

“I really just fell in love with the law,” Brown tells Entrepreneur in a new interview. “I knew I wanted to be a lawyer.”

Starting Spencer Jane

By the time Brown arrived at Vanderbilt University for undergraduate study, she had the kind of purpose most undergrads were still searching for. 

She started chasing experiences that pushed her deeper into law. As an intern at Condé Nast’s legal department, she sat in glass-walled conference rooms learning from the lawyers on staff. In Nashville, she spent long days at the public defender’s office. When she studied abroad, she found her way into law firms overseas. 

“Every internship I ever had during that time period had a legal intersection,” she says. “I really just liked the law — and any time I could weave it into my coursework, I did.”

After graduating valedictorian of her class at Vanderbilt with a Bachelor’s in Human and Organizational Development in 2018, Brown attended Harvard Law School. There, a new idea began to tug at her attention — entrepreneurship. It arrived, fittingly, through frustration rather than inspiration. On the hunt for a professional outfit that made her feel both confident and comfortable, Brown found the options impossibly dated or ill-fitting. So she did something only an aspiring founder would do: she decided to design her own line.

The result was Spencer Jane, a workwear startup born in her law school apartment, brought to life in 2020 through an Italian manufacturer. But her first big mistake was a rookie one: she mixed up American and European sizing charts. The early prototypes didn’t fit anyone. “It was a disaster,” she admits. Yet that sizing mishap marked an inflection point. It was her first true lesson in building something from scratch.

Seeing the gaps in Big Law

When Brown graduated from Harvard Law in 2022, her path seemed preordained. She landed the kind of job that law students whisper about — a coveted associate role at Cooley, the Silicon Valley powerhouse law firm known for shepherding startups into unicorns. The offer was validation, the reward for years of experience.

At Cooley, Brown was a spectator to the rapid progress of AI inside and outside the legal industry. She saw the amount of excitement AI generated internally and externally with clients. “I wanted to be a part of that,” she says. 

Brown represented more than 50 founders and advised funds deploying capital to startups, giving her an understanding of how early-stage companies interacted with the legal system. Her role involved helping founders incorporate, raise investment and hire employees. 

“I would see a common pain point where companies had just been foregoing legal until they had enough money to afford it,” Brown says. “I saw that that was tricky because there were a lot of mistakes that you could make that could have been easily prevented and ended up costing a lot more money to correct later on.”

In a world where founders can prototype products in days and iterate constantly, legal work is slower and more costly. That causes many first-time founders to find templates for legal documents on Google, experiment with tools like ChatGPT or avoid legal help altogether until a financing event forces them to confront it.

Walking away from Big Law

In May of 2025, Brown did the unthinkable. At the age of 30, after three years at Cooley, she handed in her resignation and stepped into startup uncertainty. 

Brown’s venture is Soxton, an AI-powered legal startup designed for founders at their most uncertain moment: the beginning. Instead of hourly billing and endless paperwork, Soxton delivers legal guidance in a fast, automated, and radically affordable way.

“I just went for it,” Brown says.

Soxton is still in stealth mode; its website only features a waitlist. However, Brown says that over 300 startups are already using the service. Growth has been driven almost entirely by referrals: founders can only gain access to Soxton by being referred by existing customers. 

The process of working with Soxton is simple: founders meet with Brown and the team to discuss their needs, and then can request documents or workflows. AI takes the first pass at creating a document, which is then reviewed by a human lawyer. Soxton charges $100 for a custom contract reviewed by a human attorney.

Soxton is a step up from asking ChatGPT for legal help because it adds the option of human lawyers refining and returning a contract within a few hours. “I think that AI is not in a place yet to be the only source of legal advice,” Brown says. “Right now, we have lawyers review everything that is AI-generated before it goes back to a client.”

Prediction for the future

Since launching in May, Brown has raised $2.5 million from investors and grown Soxton to a core team of four full-time employees and more than 20 contractors. Her workdays now routinely stretch past 12 hours, with most weeks crossing the 100-hour mark — more hours than she worked at Cooley. But she says it doesn’t feel like a sacrifice. “I wish for everyone to care about their job the way I care about Soxton,” she says. 

Over the next decade, Brown predicts that the legal system is going to change “significantly.”

“I think that more people are going to have access to legal services at an easier and earlier point in time in a company’s life cycle,” she says. “I’m super excited that Soxton gets to help pave that way.”

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