What We Would Tell Our Year-One Selves

In 2016, Freeman Lovell was born from a simple question: How would a law firm operate if it were designed specifically around the needs, constraints, and realities of entrepreneurs?
At the time, our founding partners, Josh Freeman and Steve Lovell, saw a significant gap. The legal industry was built for two extremes: massive global corporations or one-off individual matters. This left the small-to-mid-market entrepreneur—the engine of our economy—underserved and overcharged.
Now, during our tenth anniversary, we sat down to look back at the journey. If the 2026 versions of ourselves could sit down for lunch with the 2016 versions, here are the 10 lessons we’d share about our experience building a business.
1. Small Businesses and Small Legal Teams Pair Well
In Month One, our biggest worry was whether clients would trust a lean, entrepreneur-focused firm over a big, flashy law firm. We quickly learned the opposite: those very clients were starving for the agility that big firms couldn't offer.
The Lesson: Don't apologize for your size; lean into the responsiveness it allows.
2. Good Things Take Time: Trust the Process
In Year One, we estimated things would be easier and go faster by a factor of about three. We’ve since gained a deep appreciation for what our clients go through every day.
The Lesson: Building a brand and a reputation is a slow-burn investment. Double your timeline, triple your patience.
3. Outcomes Over Overhead
We opted for a remote-first, lean blueprint long before it was popular. We realized early on that there is a sharp distinction between essential infrastructure and optional trappings.
The Lesson: High-tier legal strategy and technology are "must-haves." Focus on investing in things that improve client outcomes.
4. Keep Your Growth in Alignment
There was a time when we grew too fast. We added attorneys and employees who weren’t truly aligned with our values, and our service levels began to suffer. We had to take a hard look in the mirror and make some difficult course corrections. But through the process, we learned so much about who we want to be, how our people and clients should be served, and what that looks like for Freeman Lovell.
The Lesson: Work with people who are aligned with your business and clients' needs.
5. Simple is Better Than Perfect
Early on, we allowed too much complexity to creep into our processes and policies in an attempt to be "perfect." We eventually learned that perfection is an impossible, exhausting quest.
The Lesson: Focus on simplicity. It allows the business to run smoother and makes you more agile when things go wrong.
6. Consider the Full Business and Legal Ecosystem
For entrepreneurs, legal questions aren't confined to a single silo. A real estate lease affects your tax structure; a hiring decision affects your IP.
The Lesson: In business, everything is connected. We can better help our clients scale when they’re able to make informed, strategic decisions at every step of the journey.
7. Vetting for "Fit" is a Non-Negotiable
If we could save our younger selves the most stress, it would be this: better evaluate the alignment of every person you invite into your circle.
The Lesson: Whether it’s an employee, a partner, or a client, if the values aren't aligned, the partnership will eventually fail.
8. Your Success is Earned Years Before the Exit
We’ve seen that a successful sale isn't won at the closing table. It’s earned through clean corporate practices, protected IP, and enforceable contracts set up years in advance.
The Lesson: Preparation changes the nature of decision-making. Early preparation makes for smoother exits.
9. Success Looks Different for Every Entrepreneur
Helping an entrepreneur means different things for each entrepreneur we work with. While there are similarities, there are so many unique needs every business has. It’s not a static service; it requires flexibility and creativity because every business has unique needs.
The Lesson: To truly serve an entrepreneur, you have to be as dedicated to their "why" as they are.
10. The Decade of Reinvention
As we enter Year Ten, the road ahead is unprecedented. AI technology is fundamentally changing what it means to be a lawyer. We expect the next ten years to be a period of experimentation and exploration.
The Lesson: There has never been a more interesting time to be in business. Don't fear the change—lead it.
To our clients and partners from the last decade: Thank you for being part of this journey! We wouldn’t be here without you.




