Master of the LBO: Private Jet King

Ted Forstmann turned a dying Gulfstream into billions.

His funds earned 55% annual returns for 19 years.

The Playbook of the Private Equity Titan⬇️ The Legend

"I like deals like I like women: big, complicated, and with a lot of surprises"

Ted Forstmann dated Princess Diana, fought Michael Milken and made Billions.

WOW!!!

@OrlandoBravoTB just dropped a masterclass on Software Private Equity

AI. Valuations. Exits.

Notes from his latest interview ⬇️ Valuations & the Dot-Com Era

AI valuations today are a bubble:

A $50M ARR company cannot be worth $10B.

To double investors’ money, it must produce $1B in free cash flow.

Even if the product is right, even if the market's right, that's a tall order.

Difference vs Dot-Com:.

Now you have some really big companies with big healthy balance sheets financing this activity, which was different than what happened roughly 25 years ago.

The Private Equity Billionaire

Henry Silverman made Billions without owning a single asset.

He turned dying brands into royalty machines

The Silverman Playbook ⬇️ The Mind of a Deal Genius

Silverman was a builder who could sell faster than he built.

Everything he owned was for sale if the price exceeded intrinsic value.

Business was a balance sheet:

Assets exist to be marked to market, not worshipped.

That detachment made him lethal.

Every empire starts with a small deal.

A.N. Pritzker bought a failing coffee-pot maker for $25K

Sold it for $23 MILLION!

That tiny deal became the seed of a $30 Billion dynasty.

If you buy below book value and wait long enough, America does the rest

The Pritzker Formula⬇️ Abram Nicholas Pritzker was a Depression-era lawyer with a taste for hard assets and harder bargains.

In 1942, while most investors hoarded cash and fear,
A.N bought a bankrupt coffee pot company for $25,000.

The Private Equity Pioneer

A broke Hebrew teacher learned to buy companies with their own money

He acquired billion-dollar empires without putting up cash

Every buyout king used his playbook

Thread🧵 Riklis arrived in America after WWII with nothing.

One professor gave him an
assignment:

Find a stock where cash per share exceeded the share price.

He realized if you could take control of such a company, you could redeploy its cash for acquisitions.

The Most Underestimated Dealmaker

Jared Kushner just pulled off Wall Street’s biggest buyout.

From Fifth Avenue to the Abraham Accords to $55B Buyout

The Dealmaking Playbook of Jared Kushner

Thread At just 26 years old, Jared Kushner bought 666 Fifth Avenue for $1.8 billion.

Thesis: Fifth Avenue retail was undervalued.

Legacy leases could be reset, potentially raising retail rents from $15m to $50–60m annually.

Months later, the financial crisis hit.

THE TEXAS GUNSLINGER

Billionaire Harold Simmons started with $5,000

He raided boardrooms, unlocked hidden billions, and rewrote the rules of LBOs.

He mastered the art of turning boring companies into Billions.

The Playbook of the LBO Pioneer

Thread Simmons wasn’t born into money.

In 1961, he scraped together $5,000 to buy a small drugstore in Dallas.

Then he borrowed $650,000 to buy a chain of seven more.

By 1973, he had built 100 stores.

He sold them for stock worth $50M.

That was his first kill.

BREAKING: Apollo just launched a new vehicle in sports finance.

When billionaires need cash for teams, they call Apollo.

Sports are the next trillion-dollar asset class.

Thread Apollo just announced the launch of Apollo Sports Capital (ASC

This is a permanent capital platform dedicated to financing teams, leagues, venues, and live events.

Amazing Blackstone Guide

Investing in the Picks and Shovels of AI

Thread

At 16, Jay Gould just wanted to escape his father’s failing farm with $5 in his pocket.

Instead, he became America’s first true Wall Street billionaire

Lessons from the Dark Genius of Wall Street Arbitrage the Law

Gould studied the NY Railroad Act of 1850 until he spotted a loophole: bonds could be swapped into stock and back again.

He used this to seize control of railroads with little cash.

The biggest buyout in history is about to drop.

Silver Lake + Saudi Arabia want to take EA private for $48B.

The Playbook behind the Deal ⬇️ Why now?

The gaming industry is at a paradoxical moment:

1. Revenues are high ($178B global market).
2. Growth is slowing.
3. Costs are rising.
4. Talent is consolidating into fewer, larger studios.

EA is simultaneously essential and vulnerable.

Private Equity & Generative AI

Vista Equity believes Gen AI is the next trillion-dollar wave in enterprise software.

Core belief: Gen AI won’t replace enterprise software. It will make it indispensable.

Here’s their Private Equity Thesis for Gen AI A private equity giant confronts the AI moment

For two decades, Vista Equity has made software its sole religion.

Now the firm is facing the question every investor asks: Is Generative AI another bubble or the next internet?

Vista’s thesis: firms that integrate Gen AI into products and processes will capture market share and expand margins.

Gen AI is not a marginal productivity tool.

It is the closest technological shock to the internet itself

End of Private Equity?

Funds are choking on unsold assets.
LPs are waiting nearly a decade for cash back.
GPs cling to marks that no buyer pays

Thread For decades, PE was a machine:

Borrow cheap. Buy companies. Sell high. Return cash. Raise bigger funds. Repeat.

That flywheel stopped in 2022 when the Fed hiked rates.

Exits dried up. Multiples collapsed. And suddenly, the industry’s promises no longer matched reality

Tech Private Equity ignored Europe for a decade.

Now 13,000+ software companies are waiting.

This is the next buyout frontier

Thread Europe now counts 13K software companies with revenues above $10M, and 4,000 exceeding $50M.

EU software spending grew 11% in 2024 and is projected at roughly 9% this year.

That’s close to ten times the region’s GDP growth rate.

Software has become one of the continent’s most reliable growth drivers.

Is $400M enough to retire?

This German mechanic turned oil tycoon, cashed out, and walked away to raise cows in the Alps.

He never studied. He never founded a company.

The masculine urge to sell your company for $400M and disappear to a farm in the Alps

Thread Ernst Prost was a refugee child & cleaned bricklayers shoes to earn his pocket money.

During school holidays, he worked on construction sites.

He completed an apprenticeship as a car mechanic and, on the side, sold swimming pools and installed the equipment.

Europe is the Goldmine?

Europe looks like a nightmare for investors: dozens of countries, languages, and laws.

That mess is a moat

Thread on CVC’s report Fragmentation = Opportunity.

Europe’s fragmentation keeps deals bilateral, local, and less competitive.

That means:
•More proprietary deals
•Lower entry multiples

The market is massive.
•$20T+ GDP
•500M+ consumers
•12,000+ companies with >$300M turnover

The 2nd largest buyout market globally, but still underpenetrated by international players.

Timeless Lessons from 200 Years of Tech Investing

Railways, Radios , Dot-Coms, and EVs show the same patterns.

Thread Breakthroughs start as a joke

Disbelief is the default response to disruption.

Every major technology was first dismissed:

Railways: “Passengers will suffocate.”
Telephone: “Impossible to transmit voice.”
Internet: “No bigger than the fax machine.”

Instant masterpiece by @ganeumann.

One of the clearest frameworks on who actually captures AI value.

Amazing essay published in @joincolossus

Here are my notes Every major fortune in modern capitalism has come from riding technological waves.

Railroads. Steel. Electricity. Cars. Microprocessors.

But not every revolutionary technology makes investors rich.

The best private equity deals look like trash to everyone else:

- Buy a broken dot-com
- Fix it in 2 years
- Sell it to Google for $3.1B

8x in 24 Months

You don’t make money buying darlings. You make money buying wrecks that still throw off cash

Thread Spotting the Opportunity

Once a dot-com darling, DoubleClick was struggling after the crash.

DoubleClick provided the software that decided which ad you see when you load a website.

It had two primary businesses, but the focus was scattered. They weren't operating at their full potential.

H&F took a hard look at what was broken:

1. The management structure was outdated.
2. The businesses were misaligned.

The SaaS Cowboys

Texas Oil patch kids turned dusty courthouse records into the world’s top energy SaaS.

Blackstone just bought it for $6.5B

A Texas startup became the world’s energy brain The idea was simple:

Oil & gas data was trapped in filing cabinets, county offices, and dusty archives.

If you could digitize it, you could give producers a competitive edge.

DrillingInfo’s mission: Bring energy into the digital age.

The Distressed Champions: Oaktree

Howard Marks built his fortune buying what others fear.

He turned a €275M loan into a €1.2B Football giant

The Investment Strategy⬇️

(Slides by ClioFinance) 1/ In 2021, Chinese conglomerate Suning Holdings was drowning in debt.

To keep Inter Milan alive during COVID, they took a €275M bridge loan from Oaktree Capital.

The collateral: Suning’s majority stake in Inter.

A high-interest lifeline… that became a trap.