How to Choose a Business Lawyer: Credentials Matter, Values Matter More

How do you choose a business lawyer?

Most people start with credentials. Where did they go to law school? Have they done deals before? Do they seem competent on paper?

Fair questions. But here’s the truth:

Shared values matter more than fancy credentials.

Because at the end of the day, you’re not just hiring a résumé. You’re hiring judgment. You’re hiring someone to help you take risks, protect your interests, and speak for you when the stakes are high.

And judgment isn’t neutral. It’s shaped by how a person sees the world.

That’s why the lawyer’s worldview matters. And why you need to choose yours carefully.

I Have the Credentials—But That’s Not the Point

Let’s get the credentials out of the way.

I went to the University of Chicago Law School. I practiced at two Am Law 100 firms. I’ve worked on major venture deals for household companies, represented both founders and investors, advised clients privately, and taught business law to law students as a tenured professor for over a decade—winning awards for it. I’ve published books and scholarly articles on private governance, startup finance, and the future of business law.

You can read my full CV here.

But credentials aren’t hard to find. What’s harder to find is a lawyer whose judgment you trust. Who shares your sense of what a good deal looks like. Who doesn’t flinch at words like “profit,” “ownership,” or “capital.”

Because—and I say this as someone who teaches in this field—a lot of lawyers working in business law have never actually believed in business. They see it as a fallback—not a calling.

What Kind of Lawyer Are You Really Hiring?

Let’s not pretend the profession is value-neutral. It’s not. It’s full of smart, well-credentialed people who fundamentally distrust the very system you’re building your business inside of.

You can hire a lawyer with an Ivy League pedigree who believes private capital should be dismantled. You can hire someone who will, on paper, “represent your interests” while quietly resenting the fact that you’re trying to build wealth.

Or, you can hire someone who respects your goals. Who believes entrepreneurship matters. Who sees business as a civic structure—not just a power play.

That’s the kind of lawyer I try to be.

What I Believe (and Why It Matters to You)

I’m a card-carrying classical liberal. I believe in private ordering—meaning, free markets are our best tools for empowering people to build a good society.

I don’t just tolerate entrepreneurship—I believe in it.
I think contracts, companies, and capital are the architecture of freedom.

I’ve written serious research papers about “Democratizing Startups”—not because it’s trendy, but because it’s necessary. If we want economic liberty to survive, we have to lower the barriers to entry and raise the quality of advice. That’s part of what I’m doing here.

So yes, I have the technical chops. But I also bring a coherent worldview to the work. 

TL;DR: I’m not a Marxist.

So How Should You Actually Choose?

Credentials are the starting point. But once you’ve cleared that bar, ask harder questions:

• Does this lawyer respect the kind of business I’m building?
• Do they believe in private enterprise—or are they just cashing in on it?
• Will they explain the law—or hide behind it?
• Do they have skin in the game—not financially, but intellectually and ethically?

These are questions about values, not degrees.
And values determine the kind of advice you’ll get when it matters most.

Bottom Line

If you’re hiring a lawyer to build your business, protect your investment, or help you negotiate terms that reflect your goals—you need someone whose worldview aligns with yours.

You need someone who:

• Respects risk but does not fear risk-taking
• Supports capitalism without apology
• Sees business as a source of human freedom—not just as a source of legal fees

That’s what I believe. That’s how I practice.
And if that resonates with you, we might be a good fit.

Want to talk through a deal or see if we align?
Click here to schedule a consultation.