The Greatest Lawyer to Ever Live

Investing Lessons from Two Attorneys

Joe Jamail was the greatest lawyer to ever live.

He was a billionaire when he died.

Jamail had an almost cartoonish aura. He was a larger than life Texan who spoke in a slang seldom heard outside the deep south. Here are some of my favorite Jamail-isms:

• “I’d rather have a nose on my ass than go to Delaware for any reason” - in response to being reprimanded by the Delaware Supreme Court.

• “Don’t be tellin’ another lawyer to shut up. That aint your goddamn job, fat boy.” - said under oath, in a recorded deposition right before attempting to engage in a fist fight with a witness. Here’s the YouTube video. It’s hilarious.

• “I would like for you to remind him that when his professional ancestors were putting leeches on George Washington to bleed him, mine were writing the Declaration of Independence” said in response to a doctor who was criticizing Jamail’s profession.

The way Jamail tells it, it’s like he fell backwards into this career.

He just showed up at the University of Texas Law School and started taking classes. He didn’t know you had to take a test to get in.

He took the bar exam on a dare. The passing score was 75. Upon receiving a 76, Jamail exclaimed, “Shit, I've over-trained!”

He tried his first case before graduating law school. The barmaid at his favorite watering-hole cut her hand while opening a bottle. “I told her we should just sue and see what happens.”

Jamail showed up in court and argued the case. Pearl Brewing offered a $500 settlement. Jamail wanted $1,000. They settled at $750, and Jamail took a 30% cut as his fee… which he spent at the bar.

From that point on, Jamail worked on a percentage basis ONLY.

He made $200 representing the barmaid.

Three decades later, he’d pull in $335 million from a single case.

One time, his musician friend Billy Joe Shaver got into a barfight and shot a man in the face. Jamail guided his friend to the proper legal counsel and advised him on strategy. Billy Joe was found innocent.

Billy Joe wrote one of the all-time-great country songs about his case, and paid homage to his friend.

The song is called “Wacko from Waco” and the first lyric goes like this:

“I’m a wacko from Waco, aint no doubt about it. Shot a man there in the head but can’t talk much about it.”

But my favorite Jamail story is told by Carl Icahn.

Joe Jamail - Pennzoil v. Texaco

In 1984 Texaco purchased Getty Oil.

But there was a problem.

Pennzoil already had a “handshake agreement” to buy Getty.

Enter Joe Jamail.

Jamail was friends with Pennzoil’s CEO, Hugh Liedtke.

At Jamail’s recommendation, Pennzoil sued Texaco for tortious interference. Pennzoil claimed it was harmed by Texaco cutting in on its bid for Getty shares.

I’m no lawyer, but this case seems pretty flimsy. Pennzoil and Getty didn’t even have a written agreement. And how do you sue somebody for topping your bid?

Anyhow, Pennzoil filed suit in Texas.

Before I tell you Pennzoil’s request for damages, let’s look at a few numbers.

In 1984, Pennzoil had a market cap ranging between $1.3 and $2.0 Billion. Here’s a quick look at the financials:

• Pennzoil earned $111MM of net income in 1984.

• Book value was $955MM.

So how much “harm” was done to Pennzoil?

Jamail stands up in the court room and claims Texaco caused $12 Billion of damages!!

WHAT?!

How can a business with a market cap of $1 - $2 Billion and $100MM of earning power be harmed to the tune of $12 billion?

Anyhow, the jury deliberates.

And when they emerge, they declare Pennzoil should be owed….

12 billion dollars.

Unbelievable.

But there’s a slight problem. Texaco is both unwilling and unable to cut a $12 billion check.

This is where Carl Icahn enters the story.

Icahn bought shares of Texaco after the price got nuked. He thought the case was likely to be settled. And so when Texaco shares fell from $60 to $25, Icahn got to buying.

Jamail and Liedtke (Pennzoil’s CEO) set up a meeting with Icahn in his New York office in hopes of moving the case along.

So in walk Jamail and Liedtke. And it goes something like this:

Jamail: “Jim Kinnear (Texaco CEO) won’t tawk to meh.”

Icahn: “Well I can understand why. He owes you $12 billion that you’re basically stealing from him”

Liedtke: “C’mon Joe, I told ya, ya cain’t tawk to this man”

Jamail: “Icahn, we gotta have 12 billyun dollas”

Icahn: “There’s no way you’re gonna get $12 billion. They don’t have $12 billion and even if they did they aren’t gonna give it to you.”

Liedtke: “I told you this Icahn was no good.”

**Liedtke storms out of the office with Jamail following. As Jamail pulls the door, he pauses, and looks back to Icahn**

Jamail: “Icahn, I think you and I can get this thang done. Let’s you and I go out and have a drank”

Icahn: “Joe, it’s 10:00 in the morning, where the hell are we gonna have drink?”

Jamail: “C’mon we can have a drank and tawk about this.”

So they relocate to a bar down the street, at 10:30 in the morning.

Now, it’s important to note one thing. Texaco wanted this deal settled so its stock would rebound. And Jamail knew deep down that the Supreme Court would throw this case out if they ever heard it. Again, how could $12 billion be the right number?

Behind closed doors, Kinnear (Texaco CEO) had told Icahn he’d give $3 billion in a settlement. Still a totally crazy number for Pennzoil to be paid, but enough to placate Texaco stakeholders and lift the stock price.

So, cut to the restaurant down the street where the conversation continues. This time it’s just Jamail and Icahn:

Jamail: “Let’s have a bottle of vodka. You and I can tawk like two men.”

**Icahn orders a bottle of vodka… at 10:30 in the morning**

Jamail: “You heard the fat man, we need 12 billyun dollas” (Hugh Liedtke was obese)

Icahn: “No way”

Jamail: “There’s no settlement here.”

Icahn: “You’re not getting $12 billion.”

Jamail leaning in: “What cannn I gettt?”

Icahn: “You can get $3 billion.”

Jamail: “I’ll deliver the fat man, if you’ll deliver Kinnear.”

And that’s how the deal was settled. Over a bottle of vodka at 10:30 in the morning.

To celebrate, they have a drink. And then another… And then another.

Now it’s noon, and people are filing in for lunch. Jamail’s kicked back with a foot up on the table, in total drunken bliss.

Jamail: “Awe, I’m happy man. I’m happy. $3 billyun dollas. I get 20% of 3 billyun. I get six hundred millyun dollas. That’s real good.”

Icahn, having a bit of fun: “Joe, what good works are you gonna do, now that you have $600 million?”

Jamail, blitzed: “Good works? What you mean good works?”

Icahn: “You know charities, soup kitchens.”

Jamail, drunkenly yelling: “I’ll tell you what I’m gonna do…

“I’M GONNA BUY P*SSY”

And that’s how Pennzoil made $3 billion.

Jamail ultimately walked away with a $335 million payday.

The greatest lawyer to ever live.

Here’s Icahn telling the full story:

A Rich Lawyer’s Diary

There’s this thread on reddit.

It’s called r/fatFIRE.

It’s just a bunch of rich people talking about their unique problems.

Fly first class or charter a plane? Buy a second home or rent? How do I leave $25MM to my kids without paying the tax man?

Stuff like that.

But there’s this guy who posts once a year. His posts are like a diary entry. It’s incredible.

He goes by calishitlawguru.

He’s a personal injury lawyer that went into business for himself in 2014.

He made $300,000 that first year.

Last year he made over $15 million.

Here’s his 2024 annual post. He’s worth $38MM now.

Some quotes on his practice and operating strategy:

• “Personal injury is the type of practice area where quality of cases really matters in terms of value. One brain damage case with a commercial policy behind it could be worth more than 200 minor impact rear end cases.”

• “Over time, I slowly narrowed my practice areas. First, I cut my practice from everything to criminal, employment, personal injury, and business litigation. Then I reduced further to criminal law and personal injury. Eventually I streamlined it to just personal injury. Having a mix of contingency, hourly, and flat fee work was great at the start for consistent cash flow. But once my contingency pipeline got full, it was clear that personal injury was the best money.”

• “One of the reasons I am so profitable is that I have very low overhead. I currently have two full-time paralegals and one part-time paralegal and my monthly business expenses are about $15,000. I do no paid marketing/advertising.”

Everyone should go read his posts.

It’s inspiring.

He goes through so many ups and downs. From starting his firm, to unbearable stress, to opening a restaurant, hiring, firing and so on.

What’s crazy, is that this guy will likely become a billionaire.

He’s 40 years old and has a $38MM net worth.

If he can save $5MM a year (less than a third of his current net income) and grow his portfolio at 8% annually, he’ll be worth $1 billion in 30 years.

Lessons Learned

Joe Jamail died a billionaire. Calishitlawguru seems like he’s well on his way to the same outcome.

The median lawyer in the United States makes $145k/year.

So what’s the difference?

Equity and leverage.

Nobody would’ve ever heard of Joe Jamail if he charged by the hour.

Jamail owned his own firm. But more importantly, he organized his affairs in such a way that he could leverage the efforts of others.

Think about it. Pennzoil, Texaco and Getty Oil spent many decades building empires. Joe Jamail never pulled a single barrel of oil out of the ground. But he was able to hitch his wagon to this behemoth and cash in.

Calishitlawguru takes a piece of the action, too. Remember, he dropped every other practice line once his contingency pipeline got full.

You’ve got to own something in this life.

Selling your time is a shitty way to get ahead.

You’ve got to have equity.

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