An Interview With Chad Silverstein
We run on the belief that business should be colorful, approachable, and human. We deliver big firm sophistication but with a sane pace and flexibility. My lawyers — especially moms — succeed in high-level deals while still able to be present for their families.
In today’s fast-paced business world, the complexity of legal matters can often be overlooked, leading to significant repercussions for businesses of all sizes. From startup ventures to established corporations, the absence of legal guidance can result in critical errors that affect growth, operations, and sustainability. These mistakes range from issues with contracts and intellectual property to compliance and employment law, each carrying the potential for financial loss and reputational damage.
As a part of this series, we had the pleasure to interview Nancy Stabell.
Nancy Stabell is the founder and lead attorney of Wood Stabell Law Group, a Nashville-based firm built on the belief that great legal work should also be good business. With more than two decades of experience spanning corporate law, commercial real estate, and mergers and acquisitions, Nancy helps entrepreneurs, investors, and growing companies make confident, strategic moves that protect what they’ve built and fuel what’s next.
Thank you for joining us. To start, could you share your “origin story” with our readers? How did you begin your career? What challenges did you face in the early days? How did you overcome them?
I like to say I was born into this work, but I also chose it very early. I’m the fourth of five generations in my family to practice law, and also the fourth of five generations in real estate. On one side, it’s real estate development; on the other, it’s lawyers. I told my parents in about third grade that I was going to law school, and I never really wavered from that.
My father encouraged me to get my MBA first, which I did. I went into a transactional law program, very focused on learning how to do deals and think in terms of economics, structure, and strategy. To this day, I practice with a “business first” mindset: we solve the business and economic questions, and then we layer in the legal work.
But on the first day of my last semester of law school, my father died suddenly and unexpectedly. At the same time, I was planning a wedding on the other side of the world. I had to change my priorities, and decided I just needed to finish law school, get married, and then rebuild my life and find my equilibrium again.
I entered private practice in the early 2000s, after spending time working in federal court. I was fortunate to work closely with senior lawyers — one of whom is still my mentor today — who brought me into complex finance and transactional work early on. I learned the business side of law by being in the room for deals that shaped how I’ve practiced ever since.
The early years weren’t easy. I entered the legal market in 2000, navigated the 2003 recession, and later lived through the 2008 financial crisis, which reshaped entire industries and legal practices. In 2010, I moved in-house during a period when the company itself was under significant pressure. Eventually, I was laid off along with much of my team. Honestly, I was relieved. Challenging seasons are part of both life and business, and I handled that one the same way I handle most hard things: one concrete step at a time.
During that time, I ended up reaching out to a man at my church who had started his own firm. After church one Sunday, he drove me to his office, walked me around, and pointed to a tiny interior closet just big enough for a desk. “You can have this for free for a few months while you get going,” he said.
Today, that little closet office has grown into a five‑lawyer firm, with plans to add more. We do sophisticated corporate and transactional work — capital raises, credit facilities, equity structures, acquisitions — with a level of humanity you just can’t get anywhere else.
Is there a particular book that made a significant impact on you? Can you share a story or explain why it resonated with you so much?
I come back to “The Four Agreements” by Don Miguel Ruiz again and again, especially the agreement “don’t take anything personally.” In my work and in life, I’m constantly dealing with people in stressful situations. It’s very easy to internalize other people’s reactions and make their behavior mean something about you: Did I handle that wrong? Are they attacking me? Is this my fault?
But most of what people do and say is a reflection of their experiences, fears, and history — often formed long before I ever entered the room. When I consciously step back, remove my ego, and remember it’s not about me, I can see the situation more clearly and objectively and help clients navigate conflict without escalating it.
Do you have a favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life or your work?
Nick Saban — “You’re going to suffer through one of two things in life: either the pain of discipline or the pain of disappointment.” Anything worth doing is not going to be easy, or everyone would be doing it. But the journey of life is setting goals for yourself and pushing yourself along.
I talk about this with business owners. Running a business is like a road trip: you have to have a destination. Where are we going? Everybody wants to jump in the car — do we have snacks, the mixtape, and the map? When you’re thinking about your partners and who’s going to be on this road trip called entrepreneurship, you must have the same vision of where you’re going and the discipline to work together to get there.
How have you used your success to make the world a better place?
When I was doing labor and employment litigation, I woke up one day and realized I didn’t like representing a negative in peoples’ lives. Even when you win your litigation, you might be glad, but you can only celebrate so much when you don’t want to be in litigation anyway.
Now, I represent opportunity. I have a firm that lets me succeed for people and my community. When my clients create jobs, build family wealth, and strengthen the local economy, I get to be part of that journey.
I also use my success to build a different kind of workplace in an industry that often burns people out. We run on the belief that business should be colorful, approachable, and human. We deliver big firm sophistication but with a sane pace and flexibility. My lawyers — especially moms — succeed in high-level deals while still able to be present for their families. Creating that environment, after living through some very toxic cultures myself, is a big part of why I do this.
I’ve also invested a lot of my time and influence in civic leadership, particularly through the Nashville Business Coalition, which I’ve helped lead for over two decades. Our focus is making sure the business community — and by extension, jobs and services for everyday Nashvillians — has a voice in Metro government. We support candidates who are thoughtful about growth, infrastructure, and fiscal responsibility.
Ok, let’s now turn to the central part of our interview. What is the most common legal mistake you see businesses make due to the lack of proper legal counsel, and what are its potential consequences?
The most common legal mistake I see is businesses being undercapitalized at the start and not having the right legal infrastructure to deal with that reality. Plenty of founders underestimate how much capital they’ll actually need. That’s a business mistake. But without proper legal counsel, they also fail to build documents that answer, What happens when we run short?
For example, you should know how additional capital will be contributed, and know what happens if one partner can put in more money and the other can’t. A business can collapse from this — and they do.
Can you share an example where early legal intervention could have significantly altered the outcome of a business dispute or challenge?
A client of mine helped start a business and was originally supposed to be the key owner and driver. Instead of hiring a lawyer at the beginning, the founders used AI to generate their operating agreement and tried to “figure it out themselves.” On paper, it looked like they had a lot of legal language, but they missed some absolutely critical provisions that any business lawyer would insist on.
Because of that, my client was diluted from about 60% ownership down to 10%, even though he’s the person the entire business is built around. There were other mistakes I’ll talk about later around intellectual property that will allow him to exit and leave the business with essentially nothing.
If there had been early legal intervention, my client would have maintained control of the business, and there wouldn’t be this backdoor they could walk out to bring the whole pile of cards down.
How do changes in digital technology and online business practices complicate legal issues for businesses without dedicated legal advice?
The biggest issue is using ChatGPT or other AI as a substitute for talking to a lawyer. I understand the urge to do DIY law with AI and templates. The problem is AI sounds confident even when it’s dead wrong. I tried it out once and had to paste in the statute from the Tennessee legislature’s website to tell an AI tool, “Here is the law — what are you talking about?” because it kept giving me the wrong answer.
Non‑lawyers don’t have the foundation to know when it’s wrong. If you don’t know the right questions to ask and you don’t understand the nuance of certain terms, you will not get the right output.
In your experience, how does the absence of legal counsel impact a business’s approach to contracts and negotiations, and what advice would you give to mitigate these risks?
With the client I mentioned above, the contracts were missing provisions no lawyer would leave out. With DIY legal work, you don’t know what you don’t know. While you can find good information on your own, these beginning errors are often much more expensive than if they’d been mitigated up front. Like they say, an ounce of prevention is worth a pound of cure when things inevitably get complicated.
My best advice is to invest as part of your startup costs in getting a professional to help you set up your foundational documents correctly. Get your governance documents, a small suite of core templates tailored to your business, and then have that lawyer spend some time educating you on what they mean. Once that relationship is in place, it becomes easy and relatively inexpensive to have them quickly review things, or to give them a call with a question.
What legal pitfalls do new businesses often overlook during their initial setup and growth phases, and how can they proactively address these issues?
New businesses tend to overlook the boring, foundational stuff, especially when working with partners. Everyone’s excited to get off the runway, relying on handshakes and friendship trust to get them through.
But handshakes are great for hello and goodbye, not for equity splits, IP, or money. If you don’t have strong core documents on who’s doing what (partners, vendors, clients), it’s like building the plane in the air, or laying down track when you’re already full steam ahead. It’s always going to be more expensive and less effective.
Have a thorough foundational agreement on who’s doing what (clients, vendors, partners). Put the relationship you think you have into a written contract, so everyone’s expectations are aligned before stress.
Here is our main question. Could you list and briefly explain “Top 5 Mistakes Businesses Make Without Legal Counsel” based on your experiences and insights? If you can, please share a story or example for each.
I’ve already touched on most of these in the previous questions, so I’ll sum it up like this:
1. They underestimate how much capital they’ll actually need
…And don’t have infrastructure in legal documents to address how to resolve that situation. Early growth almost always costs more and takes longer than expected. Founders raise just enough to get to the next milestone, without modeling what happens after that. When the business needs more capital later, you need to know what will happen if you run out, how more capital will be contributed, and how ownership changes based on who put what money in.
2. They give away too much equity too early
Some founders hand out equity to friends or early helpers without thinking through role, performance, or long-term impact. I’ve seen people get 1–5% and later aren’t doing any work for their equity, or where raising capital caused extreme dilution, or the company didn’t have the runway to raise what it needed.
3. Governance is treated like an afterthought
I see companies with no clear governance framework for what happens when people jam things up and create deadlock, how to protect minority owners, what information rights they really have, or how someone exits. The worst-case scenario goes back to the AI-generated operating agreement situation, where the owner was massively diluted to minority ownership during a restructuring.
4. Intellectual property was never properly locked down
I mentioned earlier how IP was involved in that story. Like I said, the business was built around my client. His content, training, likeness, and branding made the company what it is. But instead of contributing the IP to the LLC, they only did a license agreement. It was limited, non-exclusive, and revocable, which meant the founder could at any point terminate the license and leave a company that looked valuable on paper but didn’t actually own its core asset. Mind you, they raised capital during this time, so there’s potential for serious claims. While the path forward for my client is good for him personally in the short term, it’s disastrous for the business and its investors.
5. They rely on AI tools for legal documents without expert review.
ChatGPT‑generated contracts can sound sophisticated on the surface while missing critical protections, misapplying legal concepts, or even citing non‑existent law. At best, that means paying a lawyer later to unwind and redo everything under pressure. At worst, it means… well, if you’ve read this far, you already know.
You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.
Stable, well‑run local government is one of the best ways to improve quality of life for everyone. People have to participate. Business leaders should especially be builders of civic trust, not bystanders to politics.
So read the constitution. Revisit your basic civics. Remind yourself how a bill becomes a law. Teach this in your community — not just in schools, but workplaces, churches, neighborhood groups — so people can ask questions and go through it together.
As we wrap up, how can our readers follow your work?
The best place to follow my work is on LinkedIn, where I share insights on deal structure, governance, and the legal issues founders and business leaders tend to underestimate. I’m always finding ways to connect people across industries and communities, be it founders, investors, or fellow board members. In addition to my legal practice, I’m active in board service with nonprofit and civic organizations and regularly speak with business groups about governance, risk, and building companies that can actually scale and endure.
Thank you for these fantastic insights. We greatly appreciate the time you spent on this.
About The Interviewer: Chad Silverstein is a seasoned entrepreneur with 25+ years of experience as a Founder and CEO. While attending Ohio State University, he launched his first company, Choice Recovery, Inc., a nationally recognized healthcare collection agency — twice ranked the #1 workplace in Ohio. In 2013, he founded [re]start, helping thousands of people find meaningful career opportunities. After selling both companies, Chad shifted his focus to his true passion — leadership. Today, he coaches founders and CEOs at Built to Lead, advises Authority Magazine’s Thought Leader Incubator.
Nancy Stabell of Wood Stabell Law Group On Top 5 Mistakes Businesses Make Without Legal Counsel was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.