Stop Avoiding Your Attorney—It Could Cost You More Than You Think

Most business owners hate paying attorneys. I did too—until one meeting saved me from a six-figure mistake.

I thought I had everything under control. After all, I built my business from scratch. I knew the numbers, the clients, the team, and how to close deals. Why would I waste money talking to someone in a suit who’s never signed the front of a paycheck?

But here’s the punchline: Attorneys aren’t just expensive paper-pushers—they’re your first and best line of defense. The right one can protect your wealth, your family, your time, and your legacy.

Let’s talk about what every owner like us needs to know before we learn it the hard way.

You’re Probably Lying to Yourself About Your Net Worth

When my advisors ran the first real valuation on my business, I was shocked. I thought I knew what it was worth—I was wrong. It came in way higher than I expected.

Now, I’m the exception.

Most business owners? They think their business is worth more than it really is. They’re dreaming about $10 million exits on a $3 million operation. That creates a value gap—a dangerous illusion where you make decisions based on a future that doesn’t exist.

You need to know your true wealth. That means a formal valuation, not a cocktail-napkin estimate. Your entire future could depend on it.

Skipping the Boring Stuff Will Cost You Big

Let’s be honest: legal documents are boring. Operating agreements, buy-sell clauses, trusts, corporate resolutions—this stuff doesn’t get your blood pumping.

But you know what is exciting? Not getting sued. Not losing your business in probate. Not watching your family fight over your life’s work because you never documented your intentions.

Early on, I skipped this stuff too. I thought, “It’ll be fine.” It wasn’t.

The basics matter. If you haven’t updated your documents in the past few years—or worse, never created them—you’re sitting on a ticking time bomb.

This 30-Minute Habit Has Saved Me Tens of Thousands

Twice a year, I call my attorney for a 20- to 30-minute check-in.

We don’t overcomplicate it. I just ask, “Has anything changed that I need to know about?” In return, I’ve dodged lawsuits, cleaned up language in key contracts, and stayed ahead of legal landmines.

These check-ins don’t cost much, and they’ve saved me a fortune in mistakes I never saw coming. I’m not paying for paperwork—I’m paying for peace of mind.

If this feels like overkill, it probably means you need it.

You’re Flying Blind Without a Family Planning Meeting

Once a year, my wife and I meet with our attorney, our CPA, and our financial advisor. And yes—we bring our kids into the room.

I can already hear your reaction: “I don’t want my kids to know what we have.”

That used to be me too. I didn’t want to raise trust-fund babies. I didn’t want entitlement. But you know what happened?

My kids got clarity. They got educated. They saw what it takes to build something great. And they learned how to steward—not squander—the future.

Transparency didn’t weaken them. It strengthened them.

You’re not protecting your kids by hiding everything. You’re leaving them unprepared to carry the legacy you’re working so hard to build.

Exit on Your Terms—Not When You’re Burned Out

When I launched Heritage Investors, I wasn’t thinking about selling. But I built it with value in mind. And when the trajectory took off, I sold the company 49 months after founding it.

Why?

Because I didn’t want to wait until I was tired and stuck. I didn’t want to sell in a slump. I wanted to exit from a position of strength—and that required a strategic plan, not wishful thinking.

Most owners wait too long. They stay in the game out of habit, ego, or fear. Then something happens—a health issue, market shift, burnout—and they’re forced to sell at a discount.

Don’t wait for the sucker punch. Design your exit now—even if it’s years away.

Still, Think Attorneys Are a Waste of Money?

Let’s get real:

• “Attorneys are expensive.”
  Sure. So is a lawsuit.

• “I don’t have time.”
  Neither did I. But you’ll have even less time if you have to fix a mess you could’ve avoided.

• “I can figure it out myself.”
  That’s exactly what I said before I nearly signed a contract that wouldn’t have held up in court.

• “It’s not relevant in a small town.”
  Legal problems don’t care about your zip code. They show up where people ignore the details.

Here’s Your Playbook. Execute It.

Randy, I know you’re not one for theory. You want the steps. So here they are:

1. Get Your Business Valuated.
   Stop guessing. Know the real number. It’ll shock you—either way.

2. Audit Your Legal Docs.
   Check your operating agreement, buy-sell clauses, succession plans, and estate docs. Clean house.

3. Book Two 30-Minute Attorney Check-ins Per Year.
   Prevent fires before they start.

4. Hold a Family Planning Meeting.
   Bring your spouse, your advisors, and yes—your kids. It’ll change everything.

5. Map Out a Strategic Exit.
   Don’t wait until you’re forced. Start while you’re strong.

You Built It. Now Protect It.

You’ve poured your life into this business. You’ve sacrificed for years. You’ve bled to keep things running.

So why are you rolling the dice with your legacy?

I’m telling you—your attorney is not a cost. They’re your shield. Your guardrail. Your sounding board.

You wouldn’t hand your rifle to a first-timer and hope for the best.
So stop treating your life’s work that way.

Make the call. Ask the hard questions. Build the plan.

Because if you don’t, someone else will be cleaning up your mess—and it won’t be cheap.