From Big Law to AI: Founder Logan Brown on the Realities of Startup Life

The allure of entrepreneurship often promises autonomy, financial reward, and a fulfilling work life. However, the reality can be far more demanding. Logan Brown, founder of AI-powered legal firm Soxton, discovered this firsthand, finding she now works more hours than during her time in Big Law, despite the challenges, she says she’s “having the time of my life.”

Trading Billable Hours for Founder Responsibilities

Brown, 30, transitioned from an associate role at Silicon Valley law firm Cooley LLP to launch Soxton in June of last year. She acknowledges the shift hasn’t brought the work-life balance she lacked in her previous position. “I did not have [work-life balance] in Big Law. I am working more than I did there,” Brown told Fortune. “I’m coming from a place where people work very long, hard hours, and I’m working harder now than I ever did in my old job.”

Brown’s dedication to the legal field began early, with an internship at her hometown’s district attorney’s office before seventh grade. She continued her academic pursuits, graduating as valedictorian of Vanderbilt University in 2018 and attending Harvard Law School thereafter.

Soxton: AI-Powered Legal Services for Startups

Soxton focuses on providing AI-driven legal services to startups. The company currently serves over 300 companies, with a waitlist of 1,500 more, and emerged from stealth in December 2025 with $2.5 million in pre-seed funding led by Moxxie Ventures, with participation from Strobe, Coalition, Caterina Fake, and Flex. The firm utilizes AI to generate legal documents, which are then reviewed by human lawyers, offering a flat-fee service.

The Allure and Sacrifice of Entrepreneurship

Despite the increased workload and a temporary pay cut, Brown finds the experience profoundly rewarding. “It’s definitely scary to lose the security of a stable paycheck and be on your own,” she says. “I’m not making more money, but I do have ownership of what I’m doing… We’re able to really help, be a small part of [our customers’] journey, which is fun. That part is far more fulfilling.”

Brown isn’t alone in facing these challenges. Estimates suggest that more than two-thirds of startups fail to deliver a positive return to investors, according to the Harvard Business Review.

The Rise of AI in Legal Tech

Brown’s decision to found Soxton was informed by the growing impact of AI on the legal profession. A 2025 study by Thomson Reuters found that 80% of legal professionals believe AI will have a high or transformational impact on their firms within the next five years. Having worked with tech startups at Cooley, Brown recognized the intersection of emerging technology and legal needs.

“This technology is very real, and there’s a lot of things that uniquely right now, with my background, make sense,” Brown explains. “I don’t aim for to be a founder for being a founder’s sake. That’s a bad idea, because it’s a very hard job.”

Looking Ahead: A Transformed Legal Landscape

Brown predicts a fundamental shift in the legal industry within the next decade, driven by advancements in technology. “I describe the legal profession as like yellow pages, or Blockbuster. This technology is transformative, and there is so much funding being poured into it,” she says. “In 10 years, the legal profession and the way legal services are consumed by users [will be] fundamentally different than it is now.”