From $100M Verdict to Law Professor - Ryan McKeen's Journey

Welcome to episode 42 of The Earley Show podcast, hosted by personal injury attorney Christopher Earley! For this conversation, Chris is once again joined by Ryan McKeen, Co-Founder and Consultant at Best Era, LLC.

Check out the episode below. You can also enjoy it on YouTube, Spotify and Apple Podcasts.

In this episode, Ryan delves into his personal and professional growth, leaving his previous firm with key team members to start anew. He shares insights on modeling ten-year career blocks, the challenges lawyers face in letting go and delegating, the importance of vision for legal firms, and the evolving role of AI in the legal profession.

About our guest:
As co-founder of Best Era, LLC, Ryan McKeen brings two decades in the trenches of trial and litigation and the results to prove it. At Connecticut Trial Firm, he led his team to a landmark $100 million jury verdict and built one of the fastest-growing firms in the nation.

Ryan co-authored the best-selling Tiger Tactics series, and speaks across the country on AI, marketing, and law firm leadership, and challenge lawyers to think bigger, act bolder, and refuse mediocrity. He now is an adjunct professor at the University of Connecticut School of Law where he teaches legal entrepreneurship.

Learn more about Best Era, LLC here!

You can reach Ryan by email at [email protected].

About The Earley Show:

For nearly 20 years, Christopher Earley has successfully led a personal injury law firm in Boston. On the Earley Show, a new podcast launched in the summer of 2023, Christopher and other standout attorneys will be sharing their secrets to success, and discussing the law office management habits that have allowed their practice to thrive. If you’re looking to make better use of your time, increase daily productivity or even just spend less time answering emails, you’ll definitely want to tune in to The Earley Show.

Learn more about the Earley Law Group here!

Check out the previous episode of The Earley Show here!

The Earley Show is a part of the Answering Legal podcast network. Interested in learning more about Answering Legal? Click here to learn more about 400 minute free trial!

This podcast is produced and edited by Joe Galotti. You can reach Joe via email at [email protected].

Episode Transcript:

Intro
Chris Earley (Host): Hi everyone—welcome to another episode of The Earley Show, sponsored by our friends at Answering Legal. As always, I bring you some of the very best minds in the legal industry.

Today’s a real treat. We’ve got a returning guest—the first person I’ve ever invited back for a round two. That’s how highly I think of him. He’s a law professor, he’s energetic, and he genuinely loves helping lawyers thrive, grow, and be happy.

Ryan, I’m psyched to geek out with you. How are you, man?

Ryan McKeen (Guest): I’m doing great, Chris. How are you?

Chris: I’m so good. It’s great to see you. I feel like I see you everywhere—you’re impossible to avoid in the best way. You’re fantastic at being visible and at leveraging tech, automation, and AI. We’ll dig into all of that.

You were on the show about two years ago—right before your Hundred Million Dollar Day event in Boston, which I attended. I got a ton of value from it. I learned, I grew, and I expanded. I appreciate that—it was a great event.

It’s been about two years. Get us up to speed—what’s new with you?

What’s New & Why the Pivot

Ryan: A lot has changed. I left Connecticut Trial Firm and launched Best Era, a legal consulting company. I brought a few amazing teammates with me—Brittney (our former marketing director who produced Hundred Million Dollar Day), Allison (our COO), Marissa (one of our top paralegals), and Pam (my executive assistant who also supported marketing).

Alongside that, I started a very small personal injury practice where I personally handle a limited number of cases with Marissa’s help. And I’m now an adjunct professor at the University of Connecticut School of Law.

So I traded the CEO title for founder/co-founder, professor, and lawyer—and I’m really enjoying that mix.

Chris: Very cool. You’ve re-imagined the next chapter while keeping your trial skills sharp. What pulled you into consulting and helping other lawyers?

Ryan: It’s been a personal journey. I’m a slow learner by nature: it took me about ten years to truly figure out how to be a lawyer. When I opened my own firm, I had some early wins that masked a lot of mistakes. By 2016–2017, I was working nonstop, but the money didn’t match the hours. We even had credit-card debt. It felt like I was treading water.

I realized others had figured out the business side—so I needed to learn it. I invested in myself: I joined the Rosen Institute, learned from people like Jay Ruane and Billie Tarascio, and went all-in on growing as a business owner. That led to real results at Connecticut Trial Firm—nearly eight figures in annual revenue, a $100 million jury verdict, a ~40-person team, healthy margins.

I also shared openly along the way—co-authoring Tiger Tactics and speaking at events. In 2021/2022, Lawyerist (shout-out to Stephanie Everett) invited me to coach. Even just 5–10 hours a month, I loved it. It clicked: the next ten-year block for me should be teaching. Being an adjunct doesn’t pay the bills, so Best Era lets me teach at scale, help firms worldwide, and build again—from scratch—in a new arena. That challenge energizes me.

Hitting the Peak & Asking “What’s Next?”

Chris: I love that. And I really resonate with your “10-year blocks” philosophy. Tony Robbins says people overestimate what they can do in one year but underestimate what they can do in ten. A decade gives you room to make massive change if you stay intentional.

So Ryan, you built a thriving trial firm, got that $100 million verdict—did you feel like you’d hit the top of the mountain? Was it one of those “be careful what you wish for” moments?

Ryan: Absolutely. As a trial lawyer, that verdict was my proof of concept. I didn’t need a $200 million verdict to feel validated. I’d accomplished what I set out to do. That’s not to say I’ll never try another case—I still enjoy trial work—but I’d checked that box.

With Best Era, it became: can I do it again, but differently? Running a consulting company is a whole different mountain. Some parts are easier, some are harder. But I’m motivated by challenge. It’s like Sir Edmund Hillary’s famous answer to why he climbed Everest: because it’s there.

That resonates with me. I’d done it once with a law firm. Now the question was—can I build again, in a new space, starting from experience instead of scratch? And that excites me.

Missing the Old Climb vs. Enjoying the Founder Stage

Chris: So you climbed that mountain, reached the summit. Looking back, do you miss any of it? The grind, the uphill battle, the chaos of scaling a law firm?

Ryan: Honestly? No. Not at all.

Because I brought with me the people I valued most—my closest teammates. I still have those meaningful work relationships, but in a different structure. At Connecticut Trial Firm, I was CEO at the top of a pyramid. At Best Era, there are just five of us. It’s more collaborative, more creative.

And being small is fun. It’s like the difference between a garage band riffing in clubs versus a big band on tour with all the logistics and obligations. Big firms have to move carefully—changing software, for example, becomes a massive process because so many stakeholders are involved. At our size, we can move fast.

At my core, I’m more of a founder than a manager. I love creating, building, testing, even breaking things. At Connecticut Trial Firm, growth meant repeating the same playbook in new markets. At Best Era, the canvas is blank again. We’re inventing as we go. That’s energizing.

Chris: Right—you’ve traded in the barge for the speedboat. You’re nimble, able to pivot quickly. That’s a huge advantage.

Curiosity, Energy & Best Era’s Current Challenges

Chris: A couple things jump out about you: you’re endlessly curious and you’ve got tremendous energy. I’ve even written that he who has the most energy wins. It doesn’t matter how you define winning—energy and curiosity together are a powerful mix.

I see that with Best Era. I’m a member of the Slack channel—it’s incredible. I don’t even know how you keep up with all the resources and content you post. For any lawyer serious about growth, it’s a goldmine. You and your team are producing smart, practical, generous content. Hats off.

Now, you’re relishing being a founder again. But what’s your biggest challenge right now in getting Best Era further off the ground?

Ryan: The challenge is clarity—figuring out exactly who we are and what we offer. Every day it becomes sharper.

Our approach is to build things we wish we’d had at the firm. One of the hardest challenges at Connecticut Trial Firm was training paralegals. The best hires often came from outside the legal industry—service backgrounds where they had the right attitude but lacked legal skills. Training them while juggling 50 new cases a month was tough.

So at Best Era, we created ParEra—a personal injury paralegal training program. We offer three tiers:

1. Self-guided online courses.
2. Courses plus community support—weekly or monthly calls and a Slack group for paralegals.
3. Custom consulting—Marissa works directly with firms on training, processes, documents, workflows.

We’ve spent a year building it, consulting with firms, finding pain points, designing solutions. This fall is our big push. The big question: does it catch? If it does, how do we scale—do we hire more, expand offerings?

That blank canvas is both exciting and challenging. A law firm runs on a playbook: car accident case in, here’s the process. Consulting is much more open-ended. That freedom is the opportunity and the struggle.

The Big Themes Lawyers Struggle With

Chris: Let’s zoom out. In working with so many firms, what themes do you see—things lawyers consistently struggle with, the stuff that makes you want to wave a magic wand and fix?

Ryan: There are a few, but one stands out—lawyers won’t let go.

At firms under about $2 million in annual revenue, the owner is often saying, “I alone can do this. I alone can try the case. I alone can handle intake. I alone can implement the tech.” That mindset becomes the ceiling.

The firms that break through $3, $5 million do so because they delegate. They stop white-knuckling everything.

But the challenge doesn’t end there. Firms between $5–20 million run into a different problem: the owner or leadership team is still operating with the mindset of a smaller firm. Every level of growth brings new problems, but they keep applying old tactics. It’s like suddenly you’re in outer space but still acting like you’re in Earth’s orbit—you don’t even realize the rules have changed.

Often my role is to hold up the mirror: “Here’s what your financials show. Here’s what your team looks like. Here’s what’s working. Here’s where you’re the bottleneck.” Because that’s another huge theme—the founder or CEO can easily become the bottleneck that holds the whole firm back.

Other struggles are predictable: hiring the right people, financial management, systems, accountability. But the biggest difference-maker? Vision.

Firms with clarity of vision thrive. Firms without it tread water. I’ve seen it firsthand. Lawyers often struggle to articulate where they actually want to go. Sometimes I swap “vision” for “destination”—it’s more tangible. When firms nail that, everything else flows.

Getting Vision Out of Your Head & Into the Team

Chris: That’s huge—vision or “destination.” But here’s the challenge: how do you get that vision out of your head as the founder and into the minds of your team? How do you make sure everyone knows it and owns it?

Ryan: It’s something I had to learn the hard way.

At Connecticut Trial Firm, our original vision under EOS was to achieve a $10 million jury verdict in ten years. We hit 10x that in just five. So suddenly the question was—what’s next? Where are we going now?

To reset, I went on what I call a listening tour. I interviewed everyone on my team. I asked: Who are we? What do we do best? Where do we want to go? What should this firm be known for?

Then I worked with the leadership team to refine it and get alignment. We shortened the horizon to five years—ten felt too far. Five is tangible. You can picture the next Olympics, the next presidency.

We put the vision into words. AI tools actually helped—taking brainstorms and turning them into clear, concise statements. And we paired vision with values.

From there, it’s all about repetition. If you’re the CEO, your job is to repeat it constantly—like teaching or parenting. State of the firm meetings, onboarding sessions, Slack updates, even posters on the wall. Every initiative tied back to vision: charity work, community service, best-place-to-work awards, trial outcomes.

Repetition builds clarity. Clarity builds buy-in. And buy-in creates momentum.

Chris: I like that a lot. I’m going to use that. And I encourage every listener—if your team can’t state your destination when stopped on the street, you’ve got work to do.

Leadership, One-on-Ones & Building Authentic Connection

Chris: You know, Ryan, this reminds me of something Gary Vee says: for firms under 20 people, the owner should be doing regular one-on-ones. That’s hard, but the intimacy matters. You’ve talked about mindset and letting go—but once you let go, it’s about running with people. How do you approach that?

Ryan: When we were around 10 people, I did formal weekly 15-minute one-on-ones. Once we grew bigger, that wasn’t sustainable. So I shifted.

I delegated formal one-on-ones to others, but I never gave up “the rounds.” Walking around, checking in. Not about work—about life. Asking about a teammate’s dog, their kids, the Red Sox. I’d call people randomly on my commute or during car rides: “Hey, how are you doing?” That kind of personal touch. My goal was one meaningful contact with everyone at least once a month.

With vision conversations, those were more structured—half-hour meetings on my calendar. But day-to-day, I focused on authentic, informal connection.

Chris: That’s powerful. And I can relate—I run a mostly remote firm. It’s harder without breathing the same air. I use polls a lot—asking for leadership feedback, morale checks, making sure my team knows I care. But nothing beats real contact.

Ryan: Exactly. Surveys are fine, but nothing replaces a phone call. In fact, I think in five years a phone call will be the most valuable form of communication. When you pick up the phone and just check in, no agenda, it means a lot.

Chris: And if you’re going to do it—do it authentically. Don’t half-listen while typing on your computer. Show people you care, and they’ll want to grow with you.

Hospitality, Client Care & The “Product + Team” Focus

Chris: You talk a lot about Unreasonable Hospitality. I read it, my wife read it—we loved it. It’s more than a business book; it’s about how you make people feel. And I saw on LinkedIn that you’re even having your students read it.

Ryan: That’s right. Alongside more traditional business books, because hospitality is essential. At the end of the day, it’s about taking care of your team and your clients.

We can talk all day about AI, automation, systems, KPIs—but here’s the truth: if you focus on your clients and your people, everything else takes care of itself.

I love the book Trillion Dollar Coach. One of the takeaways is a sticky note on your desk: focus on product, focus on team. For law firms, your “product” is the delivery of legal services—being responsive, diligent, caring. Pair that with making sure your people are safe, trained, well-paid, supported. If you do those two things—clients and team—you’ll grow, you’ll profit, and you’ll have a less stressful life.

Chris: Simple but profound. Focus on the work, focus on the people. Nail that, and the rest follows.

Teaching as a Law Professor & Inspiring Students

Chris: Before we wrap, I want to ask about your role as a law professor. What’s that experience been like for you?

Ryan: Pure joy. It brings me tremendous happiness.

I’m a bit of an outlier compared to the traditional law school track. Students often imagine their careers in terms of big firms, clerkships, partnerships, maybe judgeships. I come in and challenge that. I’ll ask, “What if you started a legal tech company? What if you built your own firm differently? What if you thought like an entrepreneur from the start?”

We go deep into marketing, finance, leadership, and vision—the things I wish I’d learned in school. I’ve also brought in guest lecturers like Ryan Anderson from Filevine to talk about legal tech, and Bill Biggs to share about law firm culture. My students are getting access to knowledge and perspectives that most lawyers don’t encounter until years into practice.

One of my favorite assignments is having them build a business plan for the firm of their dreams. They might not launch it right away, but it forces them to think like builders, and it will make them better employees, associates, and bar leaders.

I’m incredibly grateful to the deans at UConn School of Law, Ebony Nelson and Molly Land, for giving me the freedom to teach in this way. They’ve told me, “Ryan, do your thing.” And that’s exactly what I do.

Practical AI Tools & the AI Era Event

Chris: You’re always looking ahead. For the lawyer who’s just dipping their toes into AI, what tools should they be confident using right now?

Ryan: For most lawyers, I think Google’s NotebookLM is a game-changer. As of today—July 2025—it can handle something like 800,000 pages of PDFs. You can search, summarize, and analyze massive sets of documents quickly and accurately.

What I love is the podcast feature: you can upload briefs or case law and then ask, “What’s the core argument here? What are the key issues?” It can generate a 20-minute audio summary you can listen to while driving or walking. That’s incredibly powerful.

And unlike some other AI tools, it doesn’t hallucinate—it stays grounded in the documents you provide. You can even toggle which documents it pulls from, so your analysis is precise.

At Best Era, we’re also launching the AI Era event in Charleston, South Carolina. It’s a two-day deep dive. Day one is talks from experts, sharing big ideas. Day two is a hackathon—rolling up sleeves and building practical AI workflows into your firm.

And we’re not just talking about tools like Clio or Filevine. We’re focused on widely available platforms like ChatGPT, Google Gemini, Perplexity, Anthropic—stuff you can start using today at minimal cost. The key is not just the tech itself, but also training your team to use it effectively.

Chris: That’s brilliant. Practical, hands-on, real world.

Where to Find Best Era, Posting Habits & Outro

Chris: For folks who want to connect with you or learn more about Best Era, what’s the best way?

Ryan: Visit bestera.io—we’re adding more content all the time. You can also find me on LinkedIn (just search Ryan McKeen) or email me at [email protected]. I’m easy to find online.

And here’s the thing: I think it’s malpractice for a lawyer not to sign up. The amount of content and resources we share—it’s like a dollar a day for access. My goal is to deliver 100x the value if you engage. I wish I’d had something like this when I was starting out with no money.

Chris: I love that. And one more question before we wrap: how often are you posting on LinkedIn?

Ryan: Pretty much every day. Some days I don’t have anything, other days I’ll have three or four ideas. But usually, daily.

Chris: Lawyers, if you’re not posting on LinkedIn, you’re already behind. Get on the bus.

Ryan, thank you for coming back for a second time. You inspire me. I love your success, and I’ll always be cheering you on. Keep doing your thing.

Ryan: Thank you, Chris.

Chris: That’s it for this episode of The Earley Show. Be sure to check out more episodes on Spotify, Apple Podcasts, and the Answering Legal YouTube channel. Thanks, everybody.