Today we’d like to introduce you to Lin Cherry.
Hi Lin, please kick things off for us with an introduction to yourself and your story.
Nobody in my family was a lawyer. Growing up, my dad’s message to me was simple: be independent and have a profession. Law became my path to a real seat at the table in business.
Once I became a lawyer, I realized how much I was drawn to the creative side. My dad worked in international business – traveling around the world, sourcing products, and navigating different markets. My mom spent three decades helping shape a home for creative expression at Jacksonville’s first public school of performing arts. I grew up with a deep appreciation for creativity and culture.
I started in international trade law and quickly realized it wasn’t for me. So I did something that made no sense on paper: I left and went into the music business. I started a label and learned the industry “on the street” – how deals actually worked, how rights were handled, how creatives and companies actually interacted. Later, I went back to a law firm to nail down the fundamentals — working in a fractional general counsel role with Wayne Huizenga’s sports group, working with professional sports teams, venues and the Florida regional sports network.
That experience opened the door to a series of in-house roles at major media companies. Along the way, I lived through a complete transformation of the media business, as global technology companies rose to power and rewrote the playbooks on how content was created, distributed, monetized, and discovered. Business models that had felt stable for decades suddenly seemed fragile. That disruption pushed me to lean into tech more directly and to stay ahead of what was coming next, rather than just reacting to it.
Joining a boutique firm like Caldera Law is very consistent with that non-linear path. It gives me more control over my destiny and lets me work closely with the people and companies I’ve proudly built relationships with over the years – helping them create, build, and structure new ventures. I really believe in following curiosity and your passion. When you care about what you’re doing, you’re simply better at it.
We all face challenges, but looking back would you describe it as a relatively smooth road?
It definitely hasn’t been a straight, smooth road.
Technology has been both the biggest challenge and one of the greatest opportunities in my career. My first real experience working with software/data engineers was at Fox Interactive (Myspace). I went in expecting something rigid and highly technical, and quickly discovered that the best engineers are actually storytellers – shaping the narrative of how we live our lives online — using code instead of words.
For a lawyer, that world can be intimidating. The technology is complex, the concepts are new, and there’s no neat, existing framework to plug into. You’re dealing with user-generated content, complex rights licensing, evolving ideas of liability and privacy, children’s safety, and now with Artificial Intelligence (AI), which is reshaping these topics in real time and creating new questions. The challenge is to understand enough of the technology to translate it into clear, practical advice in plain language. That’s still hard — and that’s exactly what makes it so compelling.
There has also been the layer of navigating all of this as a woman in law. I’ve dealt with imposter syndrome and the pressure to work twice as hard to prove myself. I’ve spent much of my career surrounded primarily by men. I’ve also had the privilege of working with some incredible women, and that community has been both meaningful and uplifting. Being able to talk openly about these challenges and dynamics and support each other through them has been essential throughout my legal career.
These experiences – as a woman in law and as a partner to creative and product-driven teams – helped me see the throughline between inclusive culture, authentic expression, and innovation. One of the most rewarding aspects of my career has been shaping culture within the legal teams I’ve led, and that work naturally evolved into a Chief Product Officer role, where I was fortunate to influence culture across the company.
One of the reasons Caldera Law appealed to me is that it feels like a place where people genuinely value authenticity and want to build something special together. There’s flexibility and a sense that we’re not just slotting into a rigid framework of “this is what a law firm is supposed to be.” We’re building a firm intentionally — one that’s as rewarding to work with, as a client, as it is to work for, as a legal talent — with plenty of room for everyone to grow.
Great, so let’s talk business. Can you tell our readers more about what you do and what you think sets you apart from others?
At Caldera Law, my practice sits at the intersection of media, technology, entertainment, and dealmaking. I work with companies that are creating content, building platforms, and pushing into new business models – often in areas where the law is still catching up to the technology.
A lot of what I do looks like a hybrid of outside counsel and fractional general counsel: structuring deals, navigating IP and licensing, thinking through platform and product issues, and helping clients understand how emerging technologies, especially AI, impact their risk profile and their opportunities.
Because my path has taken me through record labels, media conglomerates, sports, and tech, I tend to see things from both sides: the creative and the corporate, the legal and the practical. I enjoy helping clients bridge those worlds, see around corners, actively manage risk, while moving quickly and building value.
What excites me the most right now is that we’re at a moment where technology is redefining not only the business of our clients, but the practice of law itself. At Caldera, we’re leaning into AI and other tools to work smarter and more efficiently, and to pass those benefits directly on to our clients. Being in a boutique environment means I can be more nimble and partner with clients as we build what’s next.
Before we go, is there anything else you can share with us?
For nearly a decade, I’ve been part of the University of Miami’s Entertainment, Arts, and Sports Law (EASL) LLM program—now among the nation’s best, with a strong track record of placing graduates into business and legal affairs roles at high-profile media and sports organizations. That success reflects a curriculum designed to help new lawyers hit the ground running, adding value from day one.
I’m especially proud of the AI-and-dealmaking course I teach within the EASL program: “From Prompting to Purchase.” The course was born of a simple reality: AI will handle some tasks traditionally handled by junior lawyers—which means we need to accelerate the development of lawyers to handle more strategic, judgment-intensive tasks.
The capstone project for the course puts students in an associate’s shoes: requiring them to use AI to spot issues across a set of agreements and refine AI output into client-ready work product. Along the way, the course connects students with practitioners on the cutting edge of legal practice, and advances the students legal education by closing the gap between the classroom and real-world work.
The ultimate goal is to reinforce that human-centered judgment, critical thinking, ethics, and relationship building are what truly differentiate lawyers.
Contact Info:
- Website: https://www.caldera.law/
- Instagram: https://www.instagram.com/caldera.law/
- LinkedIn: https://www.linkedin.com/in/lincherry/
