Alright – so today we’ve got the honor of introducing you to Jesse Jones. We think you’ll enjoy our conversation, we’ve shared it below.

Jesse, thanks for joining us, excited to have you contributing your stories and insights. Can you talk to us about growing your team – how did you recruit the first few people, what was the process like, how’d you go about training and if you were to start over today would you have done anything differently?

At the beginning it was just me. I grew up in a family of business owners and always knew I wanted to run my own company. For the first 7-8 years out of law school, I felt stuck – I could only consistently do two of the three things I cared most about: be present with my wife and kids, build meaningful relationships with potential clients, and do interesting legal work. I thought starting my own firm would solve that tension. Surprisingly, it didn’t magically solve it. Haha. But it did give me ownership over how to build something better.

In the beginning, it was equal parts exciting and heavy. Every decision mattered. Every client conversation mattered. Every dollar mattered. There’s a unique pressure when you know that if something doesn’t get done, there’s no one else to do it. At the same time, there was clarity. I could build the kind of firm I wanted from the ground up.

My first hires were driven by pain, not strategy. I hit a point pretty quickly where I simply couldn’t do everything myself. Client work, billing, admin, marketing, operations. Something was going to break. So I hired to relieve pressure. Those first hires mostly came through relationships and referrals. I didn’t have a sophisticated recruiting funnel. I wasn’t running structured hiring campaigns. I was looking for people I trusted or who came recommended by people I trusted. The interview process was pretty informal compared to what we do today. A lot of conversations. A lot of “Can I see myself working closely with this person?” and alot of “tryouts” as I called them. I would basically pay someone to work on a few projects with me to test out the fit.

For a long time, I assumed alignment where it didn’t exist. That came from a distorted attempt at humility. I thought, “Well, I’m not that unique – surely everyone sees this the same way.” What ended up happening was that people got placed into roles they didn’t ask for, didn’t want, or weren’t wired for. That wasn’t fair to them. Eventually, I had to admit something important: no one thinks about business and leadership exactly like I do. Some people share a lot of overlap. Others share very little. And that’s not a pride issue – reality. More perspectives actually make the organization stronger. But they have to be understood and placed well. Early on, what was unconventional was how quickly I gave people responsibility. Part of that was necessity. But part of it was belief. I’ve always believed that people are capable of more than they think if you give them clarity and ownership.

That philosophy really got tested when I took a fully unplugged month-long sabbatical last year. I didn’t even bring my computer with me. That experience proved something powerful: the team could handle it. They didn’t just survive, they served our clients and each other really well. That kind of ownership culture doesn’t happen accidentally. It’s built over years of trusting people and letting them lead. Now we’re far more intentional. We use leadership assessments annually. We talk openly about culture. I’ve invested in leadership coaching. Early on, I was reacting. Now we’re building intentionally. I would hire slower and define roles more clearly. And I would be quicker to move everyone on to the next thing when there isn’t a good fit.

In the beginning, I hired to reduce pressure. Today, I would hire to advance vision. I’d spend more time defining:
What does success in this role actually look like?
What kind of wiring and temperament does it require?
What does this person need to love in order to thrive here?

I would also tell myself what I still need to hear: Chill out. Pressure doesn’t equal progress. For a long time, I operated as if carrying more internal pressure meant I was being responsible. It didn’t. It just meant I was stressed. Building a firm is a long game. Culture is built every day – whether you’re intentional about it or not. The question isn’t whether you’re building one. The question is whether you’re building the one you want. If I could go back to day one, I’d still start the firm. But I’d do it with a little more patience, a little more clarity, and a lot less self-imposed pressure.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

I’m the founder of Fourscore Business Law, a firm built specifically to serve business owners and entrepreneurs. But before I was a lawyer (or a business owner) I was a kid growing up in New Jersey in a family of entrepreneurs. I watched firsthand what it looked like to build something from scratch. I also saw the pressure that comes with signing the front of a paycheck. I’m still a huge Philly sports fan (sometimes painfully loyal), and that loyalty says a lot about me. I care about teams. I care about culture. I care about long games.

I didn’t start out on a traditional “pre-law” track. My undergraduate degree is in exercise science. I’ve always been fascinated by performance – how systems work, how people grow stronger, how incremental improvements compound over time. That mindset followed me into law and eventually into building a business. Whether it’s physical training or organizational leadership, the principles aren’t that different: discipline, consistency, recovery, and intentional growth.

I married my high school sweetheart, and we now have four kids. We’ve homeschooled them for years, and family has always been central to how I think about work. Part of why I started Fourscore was because I was personally frustrated with the limitations of practice in large corporate firms. I wanted to build a firm where excellence at work didn’t automatically mean compromise at home. We live in Raleigh, North Carolina, which we absolutely love. When I’m not working, you’ll usually find me surfing, mountain biking, or doing CrossFit-style workouts. Movement is a big part of how I reset and think. Some of my best business clarity has come mid-workout or on a trail.

Professionally, Fourscore primarily serves growth-minded business owners across a wide range of industries and stages. Our work includes business formation and structuring, contracts, employment matters, governance, risk management, and ongoing outside general counsel services. We spend a ton of time on mergers and acquisitions for businesses of all types and sizes, from founder-led companies selling for the first time to more complex strategic transactions , as well as venture financing deals for early-stage technology companies. In simple terms, we help business owners build strong legal foundations, navigate pivotal transactions, and raise capital so they can grow confidently.

Business owners live with constant pressure: legal risk, team issues, partnership dynamics, contracts, scaling decisions. We step into that complexity and bring clarity. We don’t just draft documents; we help leaders think through decisions in a way that protects the long-term health of the company. A big part of that comes from one of our core values: Don’t Be a Suit. We don’t show up as distant, overly formal technicians who hide behind jargon and memos. We think like business owners first and lawyers second. We integrate into leadership teams. We care about culture, accountability, and operational strength, not just transactions. Many of our clients see us as part of their executive team – trusted advisors who understand the business, speak plainly, and help them move forward with confidence.

I’m especially proud of the culture we’ve built at Fourscore. We’ve grown from just me to a team that can operate at a high level – even when I’m fully unplugged for a month. That didn’t happen by accident. It required intentional leadership development, annual 360 assessments, honest feedback, and a willingness on my part to grow. I’m also proud that we’re building a firm designed for longevity, for our clients and for our team. I want our work to compound over decades. I want businesses to exist and succeed years from now because we helped them build wisely early on.

If there are a few things I’d want potential clients or followers to know, they would be:
We take ownership seriously. If we’re in your corner, we’re fully in.
We believe culture compounds just like revenue does.
We are long-term thinkers. We don’t optimize for the quick win at the expense of the future.
I care deeply about growth – personal, professional, physical, spiritual. Everything (especially me) can always improve.

Ultimately, I hope people experience Fourscore as steady, principled, thoughtful, and growth-oriented. My goal isn’t just to help businesses solve legal problems today. It’s to help build companies and leaders that are still healthy and impactful decades from now.

Any thoughts, advice, or strategies you can share for fostering brand loyalty?

For us, it starts with a simple belief: business owners are people first. They have stories, families, pressure, wins, losses, and long nights. If we only interact with them when a contract needs to be drafted or a deal needs to close, we’ve missed the point. I mentioned it previously, but one of our core values is “Don’t Be a Suit.” That doesn’t mean we don’t take our work seriously. It means we don’t hide behind formality or ego. We show up as real people who genuinely care.

A big part of how I personally stay connected is handwritten notes. Every week, I write notes to new clients. Every month, I write to clients who are hitting anniversaries with us. It’s simple, but it’s intentional. In a world of automated emails and AI-generated everything, taking the time to handwrite a note communicates something different: you matter.

We also focus heavily on telling our clients’ stories. We celebrate their milestones. When they close a deal, expand locations, raise capital, or sell a company, we’re not just checking a legal box. We’re recognizing years of risk, sacrifice, and leadership. We try to reflect back to them what they’ve actually built. Practically, that looks like regular check-ins beyond active matters, proactive conversations about what’s coming next, and integrating into their leadership rhythm. We want to know what keeps them up at night and what they’re excited about three years from now.

When we handle an M&A transaction or a venture financing round, that’s a high-stakes moment. But loyalty is built in the smaller moments: knowing how particular clients prefer to communicate and doing our best to call them if they are “phone people”, being candid when something is risky, admitting when we don’t know something yet, and following through on what we say we’ll do. I also think my background shapes this. I grew up watching business owners carry real weight. I know what it feels like to be responsible for payroll. So when a client calls, I don’t see a “file.” I see a leader trying to steward something important.

Ultimately, we foster loyalty by being consistent, human, and long-term oriented. We don’t want to be the firm someone hires for one transaction. We want to be the team they trust for decades. And that kind of trust is earned one relationship, one conversation, and one handwritten note at a time.

We’d appreciate any insights you can share with us about selling a business.

Yes. I’ve sold two real estate investment and management businesses to various business partners. One of those business partners is my brother. Those weren’t nine-figure exits or headline-grabbing deals. They were real businesses, with real relationships, real cash flow, and real complexity. And going through those transactions personally shaped how I think about advising clients on exits.

One of the biggest lessons I learned is that selling a business is never just a financial transaction. It’s emotional. It’s relational. It’s tied up in identity. Most owners underestimate how much of their company’s value is tied up in themselves until they try to step away. Operational independence matters. If the business can’t run without you for at least a month, buyers will feel that risk immediately.

A few lessons that stand out from my own experience:

1. Clean financials aren’t optional. Even in smaller, relationship-driven deals, clarity builds trust. Consistent reporting and organized documentation reduce friction and speed up the time to close. The sooner you get (and keep) things in order, the more options you preserve, especially if a private equity group or sophisticated buyer ever enters the picture.

2. Buyer type changes everything. An internal buyer (partner, employee, family member) brings different dynamics than an external strategic or financial buyer. Structure, timeline, financing, and even post-sale involvement can look very different. Regardless of the structure of the deal, relationships matter alot. Especially in deals where the seller is being retained and/or is receiving some kind of rollover equity in the buyer.

3. The timeline is longer than you think. Most owners believe they can decide to sell and close in 90 days. That’s rarely reality. Between preparing books, aligning stakeholders, negotiating terms, and handling diligence, it takes time. Planning 2-3 years out gives you leverage instead of pressure.

4. Your business must be transferable, not just profitable. A buyer isn’t purchasing your hustle. They’re purchasing a system. Documented processes, diversified revenue, clear roles, and secured key employees all increase value. If the business depends entirely on your relationships or decision-making, the valuation will reflect that risk.

5. Know what “enough” means for you. Before you go to market, you need clarity on your financial needs and your life after exit. Taxes, debt payoff, and transaction costs can materially impact net proceeds. And beyond the numbers, you have to wrestle with identity. Who are you when you’re not running this company every day?

Going through my own exits reinforced something I tell clients often: the best exits are designed long before the offer comes in. If you’re hoping to sell one day, start now. Strengthen your financial reporting. Reduce owner dependence. Document your systems. Clarify your personal goals. Even if you never sell, those disciplines make you a better operator. And if you do sell, you’ll be negotiating from strength instead of reacting under pressure.

Ultimately, selling a business should be a strategic transition and not an emergency decision. The earlier you prepare, the more control you retain over how that story ends.

Contact Info:

• Website: www.fourscorelaw.com
• Linkedin: https://www.linkedin.com/in/jjonesjd/
• Youtube: https://www.youtube.com/@fourscorelaw