He Bought a Phone Number for $107,000, Sent Muffins to Lindsay Lohan Under House Arrest, and Settled a $20 Million Lawsuit for $250,000 (And This Is the Boring Part of His Resume)

Hillel Figured Out How to Own Nothing and Control Everything (Which Is Roughly What the Entire Russian Oligarchy Has Been Trying to Do, Except He Did It Legally and Without Poisoning Anyone)

“You Don’t Need to Pay Me. I’ll Work for You Free for Six Months.” The Lawyer Said No. A Few Years Later He Handed Him the Keys to the Entire Firm.

I have met a lot of unusual people in my life.

I have advised six presidents from both parties, been dropped into jungles that officially do not exist, sat in rooms where the stakes were measured in billions and in body counts, and once shared a long conversation with a legendary trader who compounded at thirty-seven percent a year by refusing to talk to anyone he did not respect.

But I had never sat across from an asset protection attorney who built his first personal fortune in law school by buying phone numbers from mortgage brokers, co-founded a gourmet muffin company with a contestant from The Apprentice, sent a dozen chocolate chip cheesecake muffins to Lindsay Lohan during her house arrest, bought a six thousand square foot inflatable laser tag arena off eBay and paid someone to drag it around state fairs in a trailer, and used all of the above as tuition for what would eventually become a law practice so unusual that he now buys and sells other law firms for sport.

Hillel Presser sat down with me on Fortunate Fishes.

By minute three I had abandoned my outline.

By minute ten I had stopped pretending I was conducting an interview and started taking notes for myself.

For those who do not know him, Hillel has spent fifteen years doing the single thing that billionaires, professional athletes, celebrities, first-generation entrepreneurs, doctors, and occasionally retired schoolteachers call him about when they realize that American society has quietly become a machine for transferring money away from people who earned it and toward people with printed business cards and contingency fees.

He describes himself as twenty percent lawyer, twenty percent friend, twenty percent psychiatrist, and the remaining forty percent is unaccounted for but probably involves a piece of commercial real estate he is about to close on.

He also describes himself, with the kind of dry precision usually reserved for war correspondents, as the lawyer who hates lawyers.

He is also, and this is important, the kid who at eight years old was buying candy at the corner store and selling it on the school bus to the rich kids at a ten-times markup. Which, if you think about it, is the purest form of asset protection there is. You cannot sue me to recover the Twix bar you already voluntarily traded me three dollars for.

Lesson 1: No Is a Timestamp, Not a Verdict.

Hillel was in his early twenties. A law student in Fort Lauderdale. He had already made more money than most practicing attorneys.

Let me explain why, because the backstory is better than the front story.

When he was in law school he bought a telephone number for one hundred and seven thousand dollars.

People looked at him like he had paid a hundred and seven thousand dollars for a haircut.

But Hillel had grown up around advertisers and he understood something most lawyers do not, which is that when a person is driving seventy-five miles an hour down I-95 and sees a billboard, they are not going to remember 585-392-5862.

He is going to remember 1-800-GREAT-RATE.

So Hillel bought 1-800-GREAT-RATE and leased it out. One mortgage broker per state. Monthly fee.

The guy in Florida paid him every month. When someone dialed the number from Florida, the call went to that broker’s cell phone. The guy in Ohio got the Ohio calls. The guy in Texas got the Texas calls.

I asked him, could you have subdivided by zip code?

He said yes, and he would have made a lot more money, but he still had to pass law school.

He was cold-calling mortgage brokers, and his pitch was a single sentence, which is how you know a man has thought about his business.

When your potential customer has three seconds to remember a phone number from an ad or a friend, will they remember your number, or will they remember 1-800-GREAT-RATE?

He was pulling in twenty to forty thousand dollars a month in recurring revenue.

In law school.

Paid off the hundred and seven thousand in three months.

Then bought thirty or forty more numbers.

One of them was 1-800-MUFFINS.

He built a whole gifting company around it, because he had done the math on 1-800-FLOWERS and decided they were targeting the wrong customer.

Flowers, Hillel observed, are a gift the wife appreciates, the husband tolerates, and the four-year-old regards as a vegetable.

A dozen chocolate chip cheesecake muffins on a reusable baking tray, however, engages the whole household.

His co-founder was a contestant from The Apprentice.

I am not making this up.

When Lindsay Lohan was placed under house arrest, they sent her a box.

The tagline was muffins taste better than flowers, and honestly, if you have to explain it, you are not the target market.

This is the kid who then decided he wanted to be an asset protection lawyer.

He walked into the Boca Raton office of Arnold Goldstein. Who at the time was the closest thing the asset protection industry had to a deity.

Goldstein had a hundred published books, forty years of practice, a publishing company called Easy Legal that predated LegalZoom by a decade, and the kind of reputation that meant Hillel could not just walk in the door.

One of maybe five or ten people in the entire country doing what he did.

Hillel wore a blue suit and a red tie.

He had studied a photograph on Goldstein’s website and figured that any man who wore a blue suit and a red tie in his professional headshot probably liked that combination.

This is what attention looks like when it has been weaponized.

They talked for an hour.

It was a good conversation.

Then Hillel made his ask.

Goldstein said no. He had just hired another attorney. Pointed down the hall. Could not step on the new lawyer’s toes.

Hillel, without missing a beat: Let me work for you free for six months. If I am not the best lawyer you have ever had, we shake hands and go our separate ways.

Goldstein said yes.

Or at least said something ambiguous enough that Hillel walked out convinced he had a job.

He FedExed a handwritten thank-you note overnight.

He followed up.

He followed up again.

A month later, Goldstein called. I can’t hire you. The new guy. His toes. I cannot step on them.

Most people go home at this point.

Hillel went home and then hired Goldstein.

Wrote him a check to be his personal asset protection attorney.

Which was absurd on two counts. Hillel was not yet thirty. And Hillel had nothing to protect.

Goldstein pointed out both.

Hillel said he did not care.

He wrote the check anyway.

The check purchased something worth more than legal work. It purchased a chair on the other side of Goldstein’s desk. Now Hillel had meetings.

Now he had a reason to be in the room.

Then he discovered there was a national asset protection conference once a year in Las Vegas.

Everyone in the field showed up.

Hillel called Goldstein’s secretary. Got the flight. Got the hotel. Got the arrival time.

Booked the same flight.

Booked the same hotel.

Timed getting a coffee in the terminal so that he and Goldstein were standing at the same espresso bar at the same moment.

Shared a cab to the hotel.

Breakfast together.

Lunch together.

Dinner together.

By the end of the conference, looking around a room of fewer than twenty attendees in the entire country, of whom maybe five did this work at scale, they had a realization.

There was no professional organization for what they did.

So they founded one.

The National Association of Asset Protection Attorneys.

Goldstein: president.

Hillel: vice president.

They flew home as partners in something.

Back in Florida, Hillel kept paying Goldstein. Kept meeting. Once a month at first. Then more.

A year and a half after the first handshake, Goldstein called Hillel in for an unscheduled meeting.

Hillel knew something was different. They had met the week before. Nothing should have been on the calendar.

Goldstein looked at him across the same desk where the first no had been delivered eighteen months earlier.

Hillel. There is a time in every man’s career to go up, and a time to go down. This is your time to go up. And my time to go down.

Hillel did not understand.

Goldstein said: It is a Hail Mary. Let’s give it a try.

Hillel still did not understand.

Goldstein said: Pretend you are on a cruise ship. And the captain died. Here are the keys to my office.

Fifty-fifty partnership.

Forty years of practice.

A hundred books.

Ten to fifteen clients a day walking through the door.

The man who would not hire Hillel for free made him a half-owner of his legal practice. Hillel closed his Fort Lauderdale practice, finished out his cases, bought his first piece of real estate in Boca Raton, and never looked back.

Here is the moral of the story.

The moral is not keep trying and the universe will reward you. That is a motivational poster. It is also a lie.

The moral is that Hillel heard no and processed it as a timestamp.

This is the answer at this moment in time.

Moments pass.

When Hillel hears no, in his own words, he hears a question: Does that mean no, not right now? Well, how about in ten minutes? If not in ten minutes, how about tomorrow?

The nine-year-old Sebastian, walking up to Jamie Foxx on a yacht in Miami while Hillel tries to pull him back, because Jamie Foxx is on a different boat at the end of the marina, says the same thing his father was too well-socialized to remember in the moment.

Dad. The worst he can say is no.

Jamie Foxx did not say no.

Jamie Foxx said walk up the stairs and get on the boat, spent twenty minutes with the kid, took pictures, took videos, talked about his movies.

Hillel admits on the podcast, with the kind of plain honesty only a secure man can offer: I was wrong. My son was right.

The nine-year-old knew it before the father did.

Most of us treat rejection as a verdict from a court whose authority we never actually examined.

Hillel treats it as a weather report.

It is raining now. Doesn’t mean it will be raining in an hour. Doesn’t even mean the person issuing the report wants it to still be raining.

Go knock on the door again.

The worst he can say is no.

Lesson 2: The Way Someone Does Anything Is How They Do Everything.

Hillel has a piece of job-hunting advice for college graduates that, by current standards, will strike about half the reading public as deranged.

Do not send a résumé by email.

Emails get lost. Emails are what everyone else sends. An email is a molecule of content indistinguishable from the ten thousand other molecules sitting in the hiring manager’s inbox.

You spent two hundred thousand dollars on your education and now you are asking for a job using the same communications channel your aunt uses to forward chain letters about Bill Gates giving away his fortune.

Instead, go to FedEx. Get thirty résumés printed on thick paper. Spiral-bound. Clear plastic cover. A hundred bucks.

You spent hundreds of thousands on the education. Spend a hundred bucks on the presentation.

Now take your printed résumé and walk to the office where you want to work.

In person.

Ask the secretary for the hiring manager.

She will offer to take the résumé and pass it along.

You will politely decline.

With all due respect, I would just like to sit here in the lobby. I don’t care if it takes five hours. If that person has a ten-second break, I would like to hand it to them personally and shake their hand.

The secretary is going to be annoyed. She is also going to tell her boss there is a person in the lobby.

At some point the boss has to use the bathroom. At some point the boss has to get coffee. At some point the boss walks through the lobby. And when he does, you are on your feet with your hand extended.

My name is John Smith. I want to come work for you. I will sweep the floors. I will wash the windows. I want to prove to you I can add value.

You might not get the job.

You will almost certainly get the interview.

Which is all you were trying to get in the first place.

Hillel attended a boarding prep school whose slogan, seared into his eight-year-old skull, was a basket of red apples with a single green apple in the middle.

The motto: In a world that teaches you to fit in, we teach you to stand out.

The sentence that organized Hillel’s entire operating system is one he repeats like a prayer:

The way someone does anything is how they do everything.

It is why he studied Goldstein’s headshot before walking in.

It is why he FedExed the thank-you note on paper heavy enough to file.

It is why, when he wanted to thank Jeffrey Gitomer (the greatest living writer on sales, author of The Little Red Book of Selling, one of Hillel’s mentors), he did not send a gift card.

He tracked down an original Steve Jobs business card.

Framed it.

Wrote a handwritten note: Just as Steve Jobs was a mentor of yours, you are a mentor of mine.

Sent it for Gitomer’s birthday.

Gitomer put it on his desk.

Then he made an entire YouTube video about it.

Told tens of thousands of his followers that his friend Hillel Presser, the asset protection attorney, had sent him this thing, and every day he looks at it and thinks of Hillel.

The card cost Hillel a few hundred bucks.

The YouTube video reached tens of thousands of the exact demographic Hillel sells to.

The relationship has paid him back for twenty years.

Same principle governs the Pappy Van Winkle story, which I am including because it is too good to leave out.

Hillel has a billionaire client in the spirits industry who had taken him and Ashley on an incredible trip.

Hillel wanted to send a thank-you.

What do you buy the billionaire who has everything?

Not a hard question for the wife, Hillel notes. You can buy her a nice bag.

But the husband?

Hillel called Pappy Van Winkle.

Not Pappy Van Winkle the brand.

Pappy Van Winkle the family.

It is a small company. He emailed. He called. He kept going until he got an actual Van Winkle on the phone.

Bought a bottle of Pappy, which is already one of the most sought-after bourbons on earth.

Then asked the Van Winkle family member to write a handwritten letter, to be sent with the bottle, reading:

From one connoisseur to another. Enjoy the Pappy.

From the Van Winkle family.

To this specific billionaire client.

I have been around wealthy people for decades.

The billionaire does not remember the bottle of Pappy.

He remembers the letter.

People in business say this kind of thing is “over the top.”

People in business are wrong.

One out of every ten people you do this for will find it excessive. That is fine.

My father used to tell me about a guy in New York City selling apples from a cart.

The guy would shout, over the sound of the city: Apple, a million dollars. Apple, a million dollars.

My father walked up to him one day and said: An apple, for a million dollars?

The man looked at him and said: I only have to sell one.

You only have to sell one.

Lesson 3: Own Nothing. Control Everything.

We now arrive at the actual law school portion of the evening.

The first thing to understand about asset protection is that most lawyers do not know it exists.

Hillel says this out loud, and it is true.

I went to Columbia Law and I never had a single class that touched the subject.

You do not get exposed to it unless someone in your family has used it, which is how Hillel first encountered it. Goldstein, the man he would later inherit, did the asset protection planning for Hillel’s parents and his uncle while Hillel was in law school.

The second thing to understand is the difference between asset protection and estate planning, which most people conflate.

Asset protection deals with life.

Estate planning deals with death.

Asset protection answers the question: while I am alive, how do I make sure what I built cannot be taken from me by a lawsuit, a creditor, an ex-spouse, a frivolous claim, or a tragic accident I did not cause?

Estate planning answers the question: when I am dead, how does what is left go to the people I love, quickly, privately, with as little siphoned off to the government and the lawyers as possible?

Asset protection comes first.

Because if you don’t protect what you have, there is nothing to pass on.

Now the meat of it.

The core technique, and there are many, but this is the clearest, is what Hillel calls owning nothing and controlling everything.

You have a rental property in your name. You get sued. You lose the rental property.

You have a rental property in an LLC. You get sued. The rental property is not yours to lose. It belongs to the LLC. The LLC did not do anything wrong.

You have two million dollars in a brokerage account in your name. You get sued. The plaintiff’s lawyer walks out with a chunk of that two million.

You have two million dollars in a brokerage account inside a limited partnership, formed in a jurisdiction with charging order protection. You get sued. The plaintiff’s lawyer cannot touch the money. By law. Literally, by statute.

All he can do is sit and wait for you to take a distribution.

Which, obviously, you never do.

You live off something else. The money compounds. The plaintiff’s lawyer bills his firm three hundred thousand dollars trying to collect and gets zero in return.

Why does this work?

Because the charging order law says, very specifically, that a creditor cannot reach in and interfere with the business of the partnership. It would not be fair to the business. Not fair to the other partners. Not fair to the enterprise.

So the law protects the partnership by refusing to let outside creditors break in.

You get the benefit.

Here is the key.

You have given up nothing.

You still control the assets. You bank wherever you want. You use any financial advisor you like. You pay no more tax. You do not sell anything.

You simply retitled.

You own nothing.

You control everything.

Hillel settled a twenty million dollar lawsuit for two hundred and fifty thousand.

Settled a five million dollar judgment for five hundred thousand.

Not because his clients were innocent.

Not because he out-lawyered the other side on the merits.

Because the other side did the math, realized Hillel’s client was uncollectible, and settled for pennies rather than spend two years in discovery chasing a ghost.

This is the principle Hillel calls creating a doubt as to collectibility.

In a normal lawsuit, both sides have a doubt as to liability. Who wins? You say you will. They say they will. Each side puts its thumb on that scale.

Hillel adds a second doubt.

Collectibility.

Even if you beat my client, what do you actually collect?

Answer: nothing.

At which point the plaintiff’s lawyer, who is (like all good predators) entirely rational about his time, stops hunting.

Because lawyers, as Hillel puts it with the affection of a man insulting his own family, are lazy. They want the easy cases. They want the settlements. They do not want to chase someone whose money is locked in a fortress.

Hillel has one line about his own profession that has stayed with me.

Across the world, there are hundreds of lawyers in every city trying to find a way to take the money you worked your entire life for. Maybe five or ten guys in the whole country help you protect it.

That imbalance is not an accident.

It is the entire reason Hillel has a business.

Lesson 4: Insurance Is Not a Plan. It Is a Coupon You May Or May Not Be Allowed to Redeem.

Before we go further, stop and look at the numbers.

One hundred million lawsuits filed in this country every year.

That number is growing.

One-in-four chance you or your business get sued in the next twelve months.

You are seven times more likely to face a lawsuit than to be in a car accident.

The average American is sued five times over the course of their life.

And the statistic I had never heard before and cannot get out of my head.

In South Florida, where Hillel practices, the divorce rate is not fifty percent.

It is, in his words, ninety-nine-point-nine percent.

He is joking.

He is also not.

So. Given all of that. What is the average American’s entire legal strategy for the statistical certainty that they will eventually be sued?

I have insurance.

Insurance is wonderful. Hillel tells everybody to buy it. He carries it himself. It is cheap. It helps you sleep.

But the insurance industry is one of the most profitable industries on earth.

There is a reason for that.

The majority of lawsuits are not covered by insurance.

Hillel tells a story on the podcast that should be tattooed on the inside of every homeowner’s eyelids.

He owns a rental. Someone gets sick inside it. They claim mold. Hillel has a ten million dollar policy. He files the claim.

The insurance company points him to a paragraph printed in four-point font on page forty-something, in which the word mold appears in the middle of a list of excluded conditions.

Claim denied.

Ten million dollar policy.

Utterly useless.

This is not an unusual story. This is the industry.

Insurance is a coupon you may or may not be allowed to redeem on the day you need it.

Asset protection is a structural fact about who legally owns your stuff.

One requires permission from a company with every incentive to deny you.

The other does not require anyone’s permission at all.

Buy the insurance.

Build the structure.

In that order, actually. Build the structure first, because the structure does not have exclusions in four-point font.

Lesson 5: Fraudulent Transfer Is Not the Problem You Think It Is.

I asked Hillel the question every law student has in the back of their head.

What about fraudulent transfer? If I know I am about to be sued, can I just move my assets into an LLC the night before and walk away whistling?

The answer is: it depends.

Which is, as Hillel notes, every lawyer’s favorite sentence.

But here is the practical reality, at least in Florida, which is where he practices.

If you are already being sued, you can still do asset protection planning.

There is actual case law saying you do not have to stand there like a deer in headlights.

If a client walks into Hillel’s office and says I just got served, Hillel can still help them. Move things. Retitle. Structure.

The risk: if you lose that lawsuit, the winning party can put you under oath, make you fill out a financial affidavit, discover your assets were moved, and file a brand-new lawsuit against you for fraudulent transfer.

If they win that second lawsuit (which costs them more money, more time, and more effort), the only remedy is to unwind the transfer. Reverse it. Put the assets back so the original judgment can reach them.

But here is the key word.

If.

In Hillel’s practice, over many years, fraudulent transfer lawsuits happen less than five percent of the time.

They are a possibility.

They are very rarely a probability.

Reason: same one that gets the original lawsuits settled cheap. Lawyers are lazy. Fraudulent transfer lawsuits are expensive, long, and hard to win. Most creditors, having discovered they cannot collect, take the settlement and go home.

One absolute rule.

If a judgment has been entered against you, if the gavel has come down and the court has said you owe this person this money, the game is over.

At that point the money is not yours. It legally belongs to the other side. No amount of retitling saves you, because you are moving something that is not yours to move.

But short of a judgment, the door is wide open.

Which means most of us, reading this on a Friday afternoon with no active lawsuit against us, have every legal option available.

The worst moment to start asset protection planning is the moment after you need it.

The best moment is today.

Lesson 6: Never Give Your Pain a Voice.

Hillel keeps a video of Jesse Itzler telling this story on standby for bad days.

He has watched it over a hundred times. He has sent it to a hundred people.

And, as it happens, Jesse will be speaking the first week of May at our R360 national conference, so if this story lands, come hear him tell it himself.

The story goes like this.

Jesse Itzler (the guy who founded Marquis Jet, married Sara Blakely the founder of Spanx, and whose life is so improbable that the mere recitation feels like exaggeration) was training for a hundred-mile race called Last Man Standing.

The rules were simple. Every runner has one hour to finish a 4.2-mile loop. When the next hour starts, you are back at the starting line, ready to go again.

50-minute loop means you get a 10-minute rest.

59-minute loop means you get nothing.

Last runner still moving wins.

Itzler, at the time, could run thirty-eight miles.

He could not break thirty-eight.

No matter what he did, he hit the wall at thirty-eight and went home and told his wife I cannot do this. I cannot get past thirty-eight.

So he does the Hillel Presser move.

He creates his own luck. He stumbles onto a podcast with a former Navy SEAL named Chadd Wright who claims he once took a guy who had never run more than five miles and walked him through a full hundred.

Itzler calls Wright.

Wright (whom Hillel notes, with the imprecision of a man who was not there personally, looks like a hillbilly from the mountains of Kentucky, long beard, covered in tattoos, eyes that have seen things you do not want to see) shows up to train him.

The real Chadd Wright, for the record, is a bearded North Georgia former SEAL. Close enough.

Wright does not do much at first. He just watches.

Then on race morning the two men sit down at the breakfast table at 4:45 AM.

Wright says: Today we are going to do three things. And if you do these three things, you are going to shatter your record.

Rule one.

We are never going to give our pain a voice.

If Wright asks Itzler how are you doing?, there is exactly one acceptable answer.

The answer is outstanding.

Not tired.

Not hurting.

Not okay.

Outstanding.

The moment Itzler says I am tired, he is tired. The moment he says I cannot do this, he cannot do this.

The moment a feeling becomes a word, the word becomes an instruction to the body.

Rule two.

We are never going to die in the chair.

Either they finish the race, or they collapse face-first on the track trying.

They do not, between laps, sit down. They do not rest. They do not wait out the pain.

They either complete the mission or they give everything and fall short in motion, not at rest.

Rule three.

We are going to be thankful.

Every single lap, Itzler has to name one thing he is grateful for.

Because it could always be better, and it could always be worse, but right now they are here. Alive. With shelter. With food. With legs that still move.

Do those three things, Wright says, and you will shatter your record.

Itzler did.

Hillel has raised two boys on these rules.

If you ask the nine-year-old Sebastian or the four-year-old Nicholas how they are today, they will say outstanding.

They will say it before they understand what it means.

Which is the point.

You install the operating system before the user knows they are running one.

That phrase Hillel kept returning to, the only reality you are limited to is your mind, is the line I took from this conversation that will stay with me longest.

The words you say out loud are not descriptions of the world.

They are instructions to the next hour of your life.

Hillel gets up every morning and says positive affirmations in the shower.

He has never once in his life asked himself am I going to be successful.

He knew.

Not a one-percent doubt.

Not a five-percent doubt.

He knew.

If you say something is going to happen, it is going to happen. If you don’t, it probably won’t.

I believed him when he said it.

I have been chewing on it ever since.

And in three weeks at R360, Jesse will say it to a room full of people who are, like me, still chewing.

Lesson 7: The Three-Dollar Rule.

If you have children, stop reading this, go find them, and teach them this tonight.

I’ll wait.

I had lunch with Hillel once and he brought Sebastian, who was seven at the time.

Sebastian was polite. Had very good manners. I figured the kid would eat his chicken fingers and stare at his iPad while the adults talked business.

Then Hillel started asking him questions.

Sebastian answered like a machine gun.

Rapid fire. No hesitation. Not showing off. Just answering, the way a kid answers when he has run the drill so many times it no longer requires thought.

Here is the three-dollar rule, which Hillel walked me through on the podcast word for word.

Sebastian gets his allowance.

Three dollars, for the sake of arithmetic.

The first dollar goes back to Dad.

Why?

Because Dad just gave him three dollars. How is this not a net-zero transaction?

Because the first dollar of every dollar you earn goes toward the cost of being alive.

Shelter. Food. Roof.

These are not optional. These are the table stakes of existence.

Before anything else, the first dollar pays for the fact that you are warm, dry, and not hungry.

This is the lesson most adults in America never learn.

Which is why a shocking number of adults in America are one paycheck away from homelessness despite having spent the previous five years taking home perfectly reasonable incomes.

They skipped dollar number one.

They went straight to dollar number three.

The second dollar is for investment.

Not spending. Not saving exactly.

Investment.

The dollar that will go out and make its own dollars, so that eventually Sebastian does not have to trade his time for money the way his father did.

When Hillel asks Sebastian what are you going to invest in?, Sebastian says real estate.

Why?

Dad, because you buy a building, and people pay you rent, and then you use the rent to buy another building.

This is a nine-year-old.

The third dollar is whatever he wants.

Candy. A toy. Something dumb. Something wasteful. Something fun.

Go nuts, kid. You earned it.

That third dollar is the reward for respecting the first two.

Teach your child these rules. Drill them until the answers come faster than the question.

You will have given them a gift more valuable than anything you could leave in a will.

Because once the first two dollars are structural, the third dollar can be anything.

Freedom. Fun. Generosity. Exploration. Risk.

But you have to pay the first two before you earn the third.

True at every scale.

Nine-year-old with an allowance. Thirty-year-old with a first real salary. Fifty-year-old selling the business. Seventy-year-old distributing the estate.

Same three rules.

Same order.

Always.

Lesson 8: The Nightclub Rule (Or, Find the Right People and Get the Hell Out of Their Way).

One thing that confused me about Hillel when I first met him is how he runs so many businesses at once.

The asset protection firm alone is a full operation.

Then the portfolio of law firms he buys and sells. The smallest had three employees. The largest had eighty.

Then the real estate.

Then the publishing company.

Then the nightclub.

Wait.

The nightclub.

Let me tell you about the nightclub.

Hillel had five or six professional athlete clients (NFL, NBA) who owned one of the biggest nightclubs in South Beach.

They had collectively invested over five million dollars.

They had lost every penny.

They were about to close it down.

Hillel walked into their office, looked at the books, and saw that despite the losses, the gross revenue was significant.

Cash flow problem.

Management problem.

Not a business model problem.

So he made them an offer.

I will write you a check right now, up front. Then I will pay you a percentage of the door, a percentage of the bar, a percentage of the valet, every single Friday. You can’t lose. Every Friday you get a check. I take the operational risk.

They took the deal.

Hillel took the club.

He ran it for a year or two.

Monday through Thursday in the law office in Fort Lauderdale. Friday after work he drove down to South Beach, had a nice dinner, and walked into the club at midnight.

The club did not open until midnight.

Here is the weirdest part of the story, which I keep thinking about.

The club made all of its money, the entire year’s profit, between midnight and six AM on Friday nights.

Hillel tried everything else.

Comedy nights during the week. Failed.

MMA cage fighting at the club. Failed.

They tried opening earlier. Different themes. Different promotions.

Nothing worked except the six hours between midnight and dawn on Friday.

But those six hours were enough.

The club carried the entire business. Athletes got their guaranteed Friday checks. Hillel got his margin. Everybody won.

When Hillel got engaged to Ashley he sold the club back to the athletes.

The building was later knocked down.

Hillel thinks it is a parking garage now.

The lesson is not that nightclubs are a good business.

Nightclubs are a terrible business.

The lesson is how a full-time practicing attorney simultaneously ran a nightclub in a different city without losing his mind.

Find the right people.

Get the hell out of their way.

Hillel put in a managing partner. Put in the right staff. Drove down on Fridays because he liked dinner in South Beach and because the owner should show up sometimes.

He was not running daily operations.

Same principle when he buys law firms.

He inserts his people. COOs, managers, staff he trusts. Lets them run it. Does not get in the weeds.

I am the visionary. I come up with the goals, the long-term objectives, the hard decisions. I do not run the day-to-day.

This is how you own twenty things at once.

You do not actually operate any of them.

You hire operators.

You check in. You set direction. You make the big calls when they come up.

And on Fridays, you have dinner in South Beach.

Lesson 9: The Hustle Is the Real Business School.

Before law school, before the nightclub, before the phone numbers, Hillel was at Syracuse.

Studying entrepreneurship, before it was even trendy.

His actual business education was happening elsewhere.

One day he saw a listing on eBay.

Six thousand square feet. Inflatable. Laser tag arena. Fifteen thousand dollars.

He bought it.

It arrived in a trailer with its own deployment system. A cart that rolled it out, inflated it, hooked into a generator.

He ran it as a business.

Private events. Birthday parties. Corporate retreats.

Then he figured out that state fairs were the real gold.

New York State Fair. Buffalo. Syracuse.

Pay an entry fee to the fair, set up your inflatable laser tag arena, and every kid who walks in pays you ten dollars.

Hillel personally hammered the stakes into the ground.

He sold bottles of water on the side, because it was hot at the fair and why leave money on the table.

He ran the thing himself at first, then eventually paid someone to travel around with the trailer.

He was also, simultaneously, buying and flipping watches.

Buying them, enjoying them for a while, selling them at a profit.

And running the candy-on-the-bus business.

And selling the phone numbers.

And going to class.

Here is what I want you to understand about this chapter of his life.

It does not matter that the laser tag business was small.

It does not matter that the watches were a side hustle.

It does not matter that the candy sold for eight cents of markup.

What mattered is that Hillel was, from the age of eight, running things.

Every one of those little enterprises was teaching him something.

Negotiating with suppliers. Managing customers. Handling cash. Delegating. Marketing. Pricing. Margin. Logistics. Risk.

By the time he sat across from Arnold Goldstein as a twenty-three-year-old, he was not a law student asking for a job.

He was an experienced entrepreneur who had chosen to also become a lawyer.

Goldstein, whether he realized it or not, was not hiring a kid.

He was inheriting a colleague.

Lesson 10: Grandma Goes to Law School.

I have to stop and tell you this one because it is too good to leave out.

Hillel’s mother was a social worker. A therapist.

Later, by her own fierce decision, a lawyer.

She was a stay-at-home mom who loved to learn.

When Hillel was in college and applying to law school, she decided, on a whim, to apply along with him.

Not to go. Just to see what the process was like. She wanted to understand what her son was about to go through.

She got in.

A Florida law school accepted her.

Then she started telling Hillel’s father that she actually wanted to go.

Hillel’s father (a dermatologist, a man who got his medical license before his driver’s license because he could not imagine affording a car) looked at his wife and said, you want to move us to Florida so you can go to law school in your fifties?

Thank God, Hillel says, his mother had also applied to Syracuse.

She went to Syracuse.

She was a first-year law student at the same university where Hillel was a senior undergraduate.

They met for lunch. They went to basketball games.

Mother and son on the same campus, separated by fifty years and two degrees.

But that is not the punchline.

The punchline is that Hillel’s mother, on her way to law school, dragged along her great-aunt.

Her great-aunt was in her eighties.

Her great-aunt also got in.

Her great-aunt became the oldest person in the history of American legal education to graduate from law school.

They wrote a book about her.

It is called Grandma Goes to Law School.

I want you to sit with that for a second.

Because every time someone tells me it is too late, every time someone says it is too late to start a business, too late to write the novel, too late to change careers, too late to learn the language, too late to marry the right person, too late to become who I was supposed to be, I am going to remember that an eighty-something-year-old woman packed up, moved to Syracuse, and started her 1L year with a torts textbook and a pencil case.

It is never too late.

Hillel lost his mother young, to Alzheimer’s.

She never got to see how her example metastasized through him.

But she planted something, and it shows up everywhere in his life.

The willingness to take on the nightclub in his thirties. The podcast appearances in his forties. The real estate acquisitions he is still making. The peer groups. The coaches. The relentless taking-on of new things.

Learning never ends, Hillel says.

His mother made sure he never forgot it.

Lesson 11: Pick a Good Wife, Have a Good Life.

Another uncle, different from the personal injury uncle, said something to Hillel when he was young that he has never forgotten.

Hillel, you can pick a good wife or you can pick a bad wife, and that will define a good or a bad life.

You don’t understand it when you’re a kid, Hillel said.

You do now.

He picked Ashley.

Ashley is Italian Catholic. Hillel is Jewish.

He grew up in a household where if he wanted a Diet Coke, he had to work for it.

She grew up in a household where she was driven home from the hospital as a newborn in a Rolls-Royce.

Yet the two cultures, as Hillel notes with the observational clarity of a man who has thought about this, have more in common than you’d think.

Both are about family. Both are about tradition. Both are about large dinners where everyone is talking at once and no one is actually listening.

Which is, I want to submit, the fundamental experience of most healthy households.

What he looked for in a wife: nice, caring, thoughtful, kind, appreciative.

What he got: someone who, he says, will literally take the earrings out of her ears and hand them to you if you say you like them.

The sub-lesson, which I almost missed because Hillel delivers it as an aside, is that when he picked Ashley he also picked her parents.

Her mother is now someone he travels with.

Let me tell you about the mother-in-law trips, because this might be my favorite part of the whole conversation.

Once a year, Hillel, his older son Sebastian, and Hillel’s mother-in-law go on a trip.

Just the three of them.

Ashley does not come.

Nicholas will come when he is a little older.

This year, Dubai.

Last year, Europe. Ten nights. Italy. France. A cruise.

Next year, possibly Japan.

Why?

Because I want my son to spend really great time with his grandmother.

Hillel’s own grandmother on his mother’s side. Grandfather on his mother’s side. Grandmother on his father’s side. All gone.

His father’s father died when his father was a young boy and Hillel never met him.

The grandparents are the asset you cannot buy more of.

There is no LLC for time with your grandmother.

So once a year, Hillel spends the money and the time, and he takes his nine-year-old to Dubai with her grandmother.

Because the grandmother who is alive this year might not be here next year.

And the grandson who is nine this year will never be nine again.

I am going to steal this tradition.

Explicitly.

I am going to steal it from Hillel Presser and install it in my own life, because I have grandchildren now, and I suspect every grandparent reading this just recognized something they have been meaning to do for years.

Do it this year.

Lesson 12: The Words You Speak Matter.

We come back, toward the end, to the Jesse Itzler video.

Because it is the thing Hillel returns to when he is having a bad day.

And because the governing principle underneath it is the principle that governs everything else.

The video is seven or eight minutes long. Hillel has watched it over a hundred times. He keeps it in the car and rewatches it between meetings when the day has gone sideways.

The core line: The words you speak matter.

You get up in the morning, and you have a choice.

Your day is going to be a good day or a great day.

Notice. Not a good day or a bad day. Hillel does not permit himself the option of a bad day.

A good day or a great day.

The only difference between the two is the words you tell yourself.

The affirmations in the shower.

The way you answer when someone asks how you are.

Your cup is not half full or half empty. There is no reality to that metaphor.

The cup is the cup.

You decide what to name it.

The only reality you are limited to is your mind.

When Hillel was in his twenties, broke and unknown and showing up on Arnold Goldstein’s doorstep in a blue suit and a red tie, he did not say I hope I become successful.

He said, to himself, I am successful. The world just hasn’t paid me yet.

Jesse Itzler’s exact line, from the video: I’m a millionaire. They just haven’t paid me yet.

Said every day, sleeping on the couches of nineteen different friends, with no money in the bank.

Until one day it was true.

I have sat in rooms where the stakes were measured in billions of dollars and classified decisions.

I have watched men and women at the absolute top of their fields. Presidents. Generals. Legendary investors. Founders who built companies from a dorm room to the S&P 500.

The common thread in every single one of them is that they decided they were going to win before any evidence existed that they would.

Then they spent years doing the unglamorous, thoughtful, relentless small things that eventually made the evidence appear.

The apple vendor in New York only has to sell one.

The kid in the blue suit only has to convince one lawyer.

The woman in her eighties only has to get into one law school.

The nightclub only has to work one night a week.

You only have to be right once.

You become right by telling yourself you already are.

Lesson 13: Time Is the Only Asset You Cannot Retitle.

I asked Hillel, at the end of the interview, the question I ask everyone on Fortunate Fishes.

What have I not asked that you want the audience to hear?

He thought about it.

Then he said something that surprised me, coming from an asset protection attorney whose entire professional life is organized around protecting financial assets.

Time. Time is the only asset that matters.

He has built a career around protecting things.

LLCs. Limited partnerships. Trusts. Charging order jurisdictions. Insurance. Fraudulent transfer statutes. Offshore structures. Real estate portfolios. Law firm acquisitions. Nightclubs, briefly.

But ask him what matters and he goes straight to the one thing no structure can protect.

You are never going to be on your deathbed saying I wish I worked an extra day. I wish I made an extra million. You are going to be saying I wish I spent one more afternoon with the people I loved.

It is why he travels with his mother-in-law and his son once a year.

It is why, when I flew to India to Ananda with my daughter Amparo last year (which I wrote about last week), I was doing what Hillel would immediately recognize as a time-asset play.

You cannot get that week back.

You cannot redo that week.

The daughter who is twenty-six this year will not be twenty-six again.

The version of you that exists in that week, with her, on that hilltop above the Ganges, is a version that will never exist again.

The whole point of the money, in the end, is to protect the time.

The whole point of the career, in the end, is to buy the time back.

The whole point of the LLC, in the end, is to make sure the time is not taken from you by someone with a subpoena and a grudge.

When I started R360, and Hillel was one of the first people to join (member number somewhere in the very low single digits), the organizing principle was exactly this.

I described it to someone once, in three words.

We are merchants of time.

That is what peer networks, done right, provide.

Time.

Because when you are stuck on something and you have a question, and you can pick up the phone and call one of fourteen extraordinary people who will solve it for you in twenty minutes, you have just bought back three months of fumbling around in the dark.

Multiply that by twenty problems a year. Multiply that by a lifetime.

The return is not measured in dollars.

The return is measured in the afternoons you got to keep.

Lesson 14: Create Your Own Luck.

One more Hillel story, because it ties everything together.

When Hillel started getting to know Jeffrey Gitomer, he did not cold-email.

He did not send a LinkedIn request.

Hillel was in the car with a friend, listening to a podcast. He did not even know who he was listening to. He just thought, this guy is smart, this guy gets it.

He was driving to the Boca Raton Resort. When he parked, he Googled some of the phrases he had just heard, and discovered the voice belonged to Jeffrey Gitomer.

Hillel had actually read Gitomer’s book years earlier.

He just hadn’t connected the voice to the author.

So he called.

The receptionist picked up. Hillel, being Hillel, was extremely warm. He started talking to her. Not about Gitomer. Just about her.

She mentioned she had a sister in Boca.

Hillel was in Boca.

They got to chatting.

The receptionist, it turned out, was Gitomer’s daughter.

Hillel befriended the daughter.

Then he befriended her sister in Boca.

He helped both of them with a few things they were dealing with.

Then he became best friends with Jeffrey Gitomer.

Look at that story and tell me what the correct word for it is.

Most people would say lucky.

Hillel happened to be listening to the right podcast. The receptionist happened to be the daughter. The daughter happened to have a sister in his town.

This is not luck.

This is what luck looks like from the outside when you are watching someone who does the right things consistently over a long period of time.

Hillel picked up the phone instead of sending an email.

Hillel was warm to the receptionist instead of bulldozing past her.

Hillel offered help before asking for anything.

Hillel followed up.

Hillel did not treat the daughter as a gatekeeper.

He treated her as a person.

Any one of those decisions, reversed, kills the outcome.

He also sent the Steve Jobs business card.

He also flew the same flight to the same hotel as Goldstein.

He also wrote the Pappy Van Winkle letter.

He also walked up to Arnold Goldstein’s office, and Jamie Foxx’s boat, and every other door a reasonable person would have walked past.

Luck, watched long enough, starts to look a lot like pattern.

And the pattern is: small, thoughtful, effortful things that most people are too lazy or too self-conscious to do.

One out of every ten people will find it over the top.

The other nine will remember you forever.

You only have to sell one.

The One Thing I Cannot Shake.

I keep coming back, since the interview ended, to something Hillel said toward the end.

In my whole life I never asked myself if I was going to be successful. I knew.

And then, almost as an afterthought:

I also never said I cannot afford that. I said, how can I afford that?

Rich Dad Poor Dad, the Kiyosaki book Hillel said he has given out more than any other, has a line about this exact move.

The poor dad says I cannot afford it.

The rich dad says how can I afford it?

The first is a statement of defeat.

The second is a question that forces the brain to start solving.

Same six words in a slightly different order.

It turns out the order is the whole ballgame.

That is the entire operating system of Hillel Presser’s life.

How do I make this work?

What structure do I need?

Who do I need to know?

What is the small, thoughtful, relentless thing I can do today that compounds into the outcome I already know is coming?

The nine-year-old Sebastian has already absorbed this. You can see it in his answers. You can see it in the way he says the worst he can say is no and walks up to Jamie Foxx’s yacht.

You can see it in the way he will, at nine, tell you without missing a beat that his second dollar is going to buy a building, and the rent from that building is going to buy another building.

Sebastian is going to be dangerous in twenty years.

Not because of the money.

Because of the words he has been taught to speak.

The Other Thing I Cannot Shake.

The R360 film experience, the one where we made a mini-documentary of Hillel’s life, his father’s life, his mother’s story, his children’s futures, went somewhere I did not expect.

Sylvia, our award-winning filmmaker, did not just fly to Florida to interview Hillel.

She flew to Rochester.

She filmed the house Hillel grew up in, which his family no longer owns.

She filmed the cemetery where Hillel’s mother is buried.

She filmed Hillel’s high school.

She filmed the spot where Hillel used to hang out with his friends in the afternoons.

She filmed the grocery store where Hillel’s family used to shop.

Then she flew down to Florida. Filmed in the house in Boca. Filmed Hillel and Ashley on the boat in Miami.

Then she filmed Ashley’s parents.

Decades from now, I hope, when Hillel is gone, his great-great-grandchildren (whom he will never meet) will sit down in a screening room and watch him explain who he was.

Where he came from. What he believed. What he learned. What he wanted them to know.

They will hear his mother’s stories. His father’s stories.

They will hear about the kid selling candy on the bus, the twenty-three-year-old in the blue suit, the muffin box sent to Lindsay Lohan, the nightclub that only worked on Fridays, the three-dollar rule, the mother-in-law trips, the fire that never dies out of a well-lived life.

That is what a life, at its best, is supposed to produce.

Not money.

Money is a means.

The life is the thing.

And Hillel Presser, who has built his entire career teaching people how to protect money, will tell you without hesitation, if you ask him the right question, that the money is there to protect the life.

Not the other way around.

Which is, if you think about it, the most radical thing an asset protection attorney could possibly say.

Now. I have given you fourteen lessons, a nightclub, a muffin box, a great-aunt, a contestant from The Apprentice, and a Navy SEAL who may or may not be from Kentucky.

What I have not given you is Hillel himself.

Which is the one thing I cannot fix with a keyboard.

You can read the three-dollar rule in print. It is not the same as hearing a man describe, with visible pride, his nine-year-old son rattling off the answers like a machine gun.

Also, I talk. I laugh. I occasionally interrupt.

You get a sense, in ninety minutes, of why this guy ends up at other people’s dinner tables on three continents.

So watch the full episode below.

Make a drink. Put your feet up. Ignore your email, which is, statistically, not as important as you think it is.

The podcast is free, unlike almost everything else in this country that is worth anything.

If this interview brought you value, please:

❤️ Hit the heart. It tells the algorithm to put this in front of someone who needs it.

🔗 Share it with one person. Not your whole contact list. The one person who would read it twice. The one person who is about to be sued, or who hasn’t taken his grandmother on a trip, or whose nine-year-old is getting an allowance this week.

♻️ Restack it. Put it in front of your own readers with your name on it. Tell them: I read this. It mattered. You should too.

💬 Leave a comment. Tell me the no you turned into a yes. Or the grandparent you still have time to see. Or the first dollar that you, maybe for the first time in your life, are going to put toward the roof instead of the third thing.

May the Mischief be with you.

Charlie

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