Jordan Belfort

Belfort's original "investing style" was securities fraud — buying penny stocks in bulk, artificially inflating prices through high-pressure sales, then dumping shares on unsuspecting retail investors. This is a pump-and-dump scheme, and it's a federal crime.

His current advice is more conventional. He now recommends long-term investing in quality companies, diversification, and avoiding get-rich-quick schemes — which is a bit like an arsonist giving fire safety tips, but the advice itself is actually sound.

He talks a lot about the psychology of selling — both in business and in how Wall Street sells products to retail investors. His main message: the system is rigged against retail investors, and the best defense is financial education.

He's not wrong about this, even if he was personally one of the people doing the rigging.

Bill Gates

Gates invests through Cascade Investment LLC in established, cash-generative businesses — railroads, waste management, agricultural equipment, farmland. His biggest single Cascade holding for years was Canadian National Railway.

He has sold most of his Microsoft stock over time. His investment philosophy outside Microsoft mirrors Buffett's: durable businesses with pricing power, bought at reasonable prices.

Jordan Belfort

Belfort's current financial philosophy is essentially: don't do what I did. Be ethical.

Build real businesses that create real value. Invest for the long term.

Don't chase shortcuts.

More specifically, he teaches that sales skills are the most valuable financial skill anyone can develop. His argument: everything in life is a sale — getting a job, raising capital, convincing a partner to join your startup.

If you can sell, you can always make money.

He also stresses the difference between income and wealth. At Stratton, he had massive income but zero real wealth — it all went to drugs, toys, legal fees, and restitution.

Real wealth, he says, is about building assets that generate income while you sleep.

On the market itself: he thinks most retail investors should stick to index funds and avoid individual stock picking. He believes actively managed funds mostly underperform because of fees.

Coming from a guy who ran a boiler room, this is actually pretty good advice.

Bill Gates

His core framework: read obsessively, think long-term, and separate emotion from analysis. He takes annual Think Weeks — solo retreats to a lake cottage in the Pacific Northwest where he reads papers and books for two weeks with no interruptions.

He publishes a reading list twice a year at gatesnotes.com. He has said that the best investment he ever made was paying $100,000 to take Warren Buffett to dinner every year.

Jordan Belfort

In his Stratton days, his risk tolerance was effectively infinite — he was leveraging illegal schemes and spending money faster than he made it. There was no risk management because the "strategy" was fraud.

Now, he describes himself as much more conservative. He's said he keeps a significant cash reserve, invests in real estate, and avoids anything he doesn't fully understand.

Prison will do that to you.

He's also said that true risk isn't financial — it's ethical. The real risk he took wasn't losing money; it was losing his freedom, his family, and his reputation.

He frames his entire cautionary tale around this idea: the biggest risk in any deal isn't the money, it's whether you can sleep at night.

Bill Gates

Gates's risk tolerance is intellectual and deliberate rather than impulsive. He takes genuinely large bets — TerraPower on nuclear fission, billions into climate technology, the Gates Foundation's campaigns to eradicate diseases that kill millions — but only after intense research.

His Think Weeks exist to force slow, rigorous thinking on big decisions. At Microsoft, he kept enough cash on hand to run the company for a full year with zero revenue because he never wanted short-term survival pressure to force a bad long-term decision.

That discipline carries into his personal finances.

Jordan Belfort

During the Stratton years, Belfort's spending was legendary and absurd. He owned a 167-foot yacht (originally owned by Coco Chanel) that he sank off the coast of Sardinia.

He had a helicopter he crashed while high on Quaaludes. He owned multiple mansions.

He spent an estimated $700,000 per week on drugs alone. He literally threw money around.

Post-prison, his lifestyle is more restrained — but still comfortable. He lives in a beachfront property in Manhattan Beach, California.

He drives luxury cars. He dresses well.

He travels for speaking gigs constantly.

He still owes restitution — $110 million to the victims of his fraud. He's paid back roughly $14 million as of the most recent public records.

The movie deal alone reportedly earned him over $1 million. His victims have pointed out, with some justification, that he's profiting from the story of how he robbed them.

Bill Gates

He wakes up early, exercises on a treadmill while watching documentaries, and reportedly does the dishes every night. He has said dishes are meditative.

For a man worth $130 billion, the emphasis on routine is either deeply grounded or very good PR. He drove himself to work at Microsoft for years and lived in a normal house long after he could afford otherwise.

Jordan Belfort

The movie deal is probably the biggest "win" of his post-prison life. Selling the rights to Scorsese and having Leonardo DiCaprio play you is a level of rehabilitation that most convicted felons can only dream of.

The film made $392 million globally and turned Belfort into a household name — in a weirdly aspirational way.

At Stratton, the raw numbers were staggering: he was reportedly earning $1 million per week at the firm's peak. But since most of that money was obtained through fraud and was subsequently seized or spent, it doesn't really count as a "win" in any legitimate sense.

His Straight Line Selling system is a legitimate post-prison success. He built a multimillion-dollar training business from a prison cell, essentially monetizing the one skill that was genuinely his: the ability to sell anything to anyone.

Bill Gates

Microsoft Windows. The decision to license MS-DOS to IBM for the PC while retaining the right to sell it to other manufacturers was arguably the most lucrative business decision in tech history.

Every PC manufacturer then licensed Windows. Gates captured the entire PC market without building the hardware.

By 1999, Microsoft's market cap hit $616 billion.

Jordan Belfort

The whole thing. Stratton Oakmont defrauded roughly 1,500 investors out of approximately $200 million.

Belfort personally pleaded guilty to securities fraud and money laundering. He was sentenced to 4 years in federal prison (served 22 months), ordered to pay $110.4 million in restitution, and was banned from the securities industry for life.

He lost everything — his money, his first marriage, his freedom, and very nearly his life (he overdosed multiple times during the Stratton years). His 167-foot yacht sank in a storm off Italy.

His helicopter was destroyed when he tried to land it on his lawn while high.

The lesson he teaches now: "I was the richest man I knew, and I was the most miserable. Money made through dishonesty isn't wealth — it's a ticking bomb." Whether you believe his redemption arc is genuine or just another sales pitch is up to you.

Bill Gates

Missing the internet. Microsoft was late and initially dismissive of the internet as a platform.

Gates eventually course-corrected and wrote the Internet Tidal Wave memo in 1995, redirecting the entire company toward internet strategy. But the delay allowed Netscape to establish footholds, and Microsoft's browser monopoly tactics led to the landmark antitrust case United States v.

Microsoft in 2000, which threatened to break up the company.

Jordan Belfort

Jordan Belfort grew up in Queens, New York. His parents were both accountants — middle class, nothing flashy.

After high school, he briefly tried selling Italian ices on the beach (made $20,000 in one summer, which gave him the taste) and then went to dental school at the University of Maryland. He dropped out on the first day after a professor told the class that the golden age of dentistry was over.

He drifted into Wall Street in the late 1980s. His first job was at L.F.

Rothschild, where he was trained as a stockbroker. He was literally on the job for his first day when Black Monday hit — October 19, 1987, the biggest one-day market crash in history.

He was immediately laid off.

So he pivoted to selling meat and seafood door to door on Long Island. No joke.

He was good at it — reportedly earning $3,000–$4,000 a week. But the stock market kept calling.

In 1989, he co-founded Stratton Oakmont, a brokerage firm in Lake Success, Long Island.

Stratton Oakmont became one of the most notorious boiler rooms in Wall Street history. The firm specialized in penny stock fraud — buying huge blocks of cheap, nearly worthless stocks, then having an army of aggressive salespeople call investors and push the price up through manipulation.

Once the price was inflated, Belfort and his partners would dump their shares. Classic pump-and-dump.

At its peak, Stratton Oakmont had over 1,000 brokers and was moving millions of dollars daily. Belfort was making an estimated $1 million per week.

The office was famous for its insane culture — drugs, parties, dwarf-tossing contests, and an atmosphere that made a frat house look like a monastery.

The SEC and FBI were circling for years. Stratton was shut down in 1996.

Belfort was indicted in 1998 for securities fraud and money laundering. He cooperated with the FBI (wore a wire to help catch other fraudsters), pleaded guilty, and was sentenced to 4 years in federal prison.

He served 22 months at a minimum-security facility in Nevada.

After prison, he reinvented himself. He wrote two memoirs — "The Wolf of Wall Street" and "Catching the Wolf of Wall Street." Martin Scorsese turned the first one into a movie starring Leonardo DiCaprio in 2013.

The film grossed $392 million worldwide and turned Belfort from a convicted felon into a celebrity. He now runs a sales training company and charges $50,000–$100,000 per speaking engagement.

Bill Gates

Bill Gates was born in Seattle in 1955. He taught himself to program on a PDP-10 at age 13.

He enrolled at Harvard in 1973, dropped out in 1975, and moved to Albuquerque with Paul Allen to found Microsoft. Their break came when they licensed an operating system to IBM for the original PC — and crucially, retained the rights to sell it to anyone else.

That decision made Microsoft. Windows became the standard operating system for the world.

Gates became the world's richest person in 1995 and held that title for much of the next 15 years. He transitioned out of Microsoft's day-to-day around 2000 and fully moved into philanthropy via the Gates Foundation.

Jordan Belfort

Stratton Oakmont was the main act — a brokerage firm that was really a fraud factory. At its peak, it employed over 1,000 stockbrokers and took dozens of companies public (most of them worthless or nearly so).

The firm was shut down by regulators in 1996 after years of violations.

His current company is Jordan Belfort Global — a sales training and motivational speaking business. He teaches his "Straight Line Selling" system, which is essentially the sales methodology he developed at Stratton, minus the illegal parts.

He sells courses, coaching, and live events.

He's also been involved in crypto promotion — he's given talks and endorsements for various blockchain projects, which is ironic given that his original crime was essentially selling worthless assets to unsuspecting buyers. He's been criticized for this, and he's pushed back by saying crypto itself isn't a scam, just some of the projects are.

Bill Gates

Microsoft (co-founder, former CEO and chairman). Cascade Investment LLC (his personal investment vehicle).

Bill & Melinda Gates Foundation (co-chair). Major holdings through Cascade include Canadian National Railway, Deere & Company, and significant farmland.

Early Microsoft equity remains a massive portion of his net worth.

Jordan Belfort

Belfort attended American University in Washington, D.C., where he earned a degree in biology. He then enrolled in the University of Maryland School of Dentistry but famously dropped out on the first day.

No MBA, no finance degree, no Series 7 at the time — he got into Wall Street purely through hustle and the ability to sell.

Bill Gates

Harvard University — studied mathematics and computer science. Dropped out in 1975 after his sophomore year to found Microsoft.