Robert Kiyosaki

Kiyosaki preaches cash flow investing — specifically buying assets that generate regular income rather than saving money in a bank account or buying a primary home. His preferred vehicles are rental real estate, businesses, and paper assets that pay dividends or royalties.

He is a strong advocate of using debt to buy income-generating assets — what he calls "good debt" — and is deeply skeptical of traditional employment, 401(k) plans, and mutual funds. He has been a vocal Bitcoin and gold advocate since the 2010s.

Scott Galloway

Galloway's personal investing style is relatively conservative given how loud he is. He keeps a heavy allocation in index funds and real estate.

He does make concentrated bets on individual stocks when he has conviction — he famously held Amazon for years. He angel invests occasionally but is not prolific.

His real wealth comes from business exits and media income, not portfolio management.

Robert Kiyosaki

Kiyosaki's philosophy has three core ideas that remain genuinely useful regardless of his personal track record. First: know the difference between assets and liabilities — assets put money in your pocket, liabilities take it out.

Second: work to learn, not to earn — early in your career, prioritize skills and financial education over salary. Third: make your money work for you rather than working for money.

These ideas are valuable. His specific execution advice — leveraged real estate, skip the 401(k), buy gold and Bitcoin — requires much more context.

Scott Galloway

Diversify, own assets, and do not confuse being smart with being lucky. Galloway preaches that the most reliable path to wealth is boring — buy index funds, own property in growing cities, and let time do the work.

He is deeply skeptical of anyone who claims they can consistently beat the market.

Robert Kiyosaki

Kiyosaki advocates for high-risk, high-leverage real estate investing that is completely inappropriate for most people who read his books. He has been blunt about this: he believes the risk of doing nothing — staying in a job, saving money, living paycheck to paycheck — is greater than the risk of borrowing to invest.

He recommends using other people's money (debt) to build wealth, which amplifies both gains and losses. His approach requires significant financial sophistication to execute safely, which most of his readers do not have.

Scott Galloway

Moderate. Galloway has experienced the full spectrum — he had a company go public and then go bankrupt (Red Envelope), which taught him that financial ruin is always closer than you think.

Post-L2 sale, he became much more conservative. Heavy real estate holdings in New York and Florida.

He preaches diversification publicly and mostly follows his own advice, with occasional concentrated stock positions.

Robert Kiyosaki

Kiyosaki lives in Scottsdale, Arizona, and has properties in various locations. He and his wife Kim have built their real estate portfolio over decades.

He drives luxury vehicles and does not live modestly. He has been transparent that he practices what he preaches on cash flow — he says he stopped working for money decades ago and lives off investment income.

He is active on Twitter/X and posts aggressively contrarian takes on the economy, dollar collapse predictions, and Bitcoin.

Scott Galloway

Galloway owns significant real estate in New York and Florida. He talks openly about his wealth and spending — nice apartments, good restaurants, private school for his kids.

He is not frugal and does not pretend to be. But he is very intentional about where money goes.

He has said his biggest financial luxury is "buying back his time" — paying for convenience so he can focus on what matters.

Robert Kiyosaki

"Rich Dad Poor Dad" is the win that dwarfs everything else. Published in 1997, rejected by mainstream publishers, it became the best-selling personal finance book of all time with over 40 million copies sold.

It changed the financial vocabulary of an entire generation — introducing concepts like assets vs. liabilities, cash flow, and passive income to millions of people who had never thought about money that way.

The royalties alone have made Kiyosaki wealthy. The cultural impact is impossible to fully measure.

Scott Galloway

Selling L2 to Gartner for an estimated $134 million in 2017. He built L2 into the go-to benchmarking firm for digital competence of luxury and consumer brands.

The exit, combined with his media career taking off simultaneously, catapulted him from "NYU professor" to "famous rich guy who yells about tech on the internet."

Robert Kiyosaki

The 2012 bankruptcy of Rich Global LLC — ordered to pay $24 million to the Learning Annex after a contract dispute, then filing for bankruptcy — was the most public failure. He has also made repeated dire economic predictions (dollar collapse, housing crash, stock market implosion) that have not materialized on the timelines he predicted, which has damaged his credibility with more sophisticated audiences.

His advice to "just buy real estate" has also stranded some followers who followed the playbook without the financial cushion to survive downturns.

Scott Galloway

Red Envelope. Full stop.

Galloway has been brutally honest about this — he took a gift e-commerce company public, it was valued at hundreds of millions, and then it went bankrupt. He has called it the most painful experience of his career and has said it took years to emotionally recover.

He lost a significant amount of personal wealth in the collapse.

Robert Kiyosaki

Kiyosaki was born in Hawaii in 1947, the son of a schoolteacher — the "poor dad" of the book's title. After graduating from the US Merchant Marine Academy, he served in the Marine Corps as a helicopter pilot in Vietnam.

He then tried several business ventures, most of which failed, including a Velcro wallet company that went bankrupt. He worked in Xerox sales, where he learned to pitch and was apparently good at it.

His real education came from his friend's father — the "rich dad" — a Hawaii businessman who taught him about cash flow, assets, and building income outside of a paycheck. Whether "rich dad" was a real person or a composite has been debated endlessly.

Kiyosaki has never confirmed his identity. In 1997 he self-published "Rich Dad Poor Dad" after mainstream publishers rejected it.

Sharon Lechter, a CPA and businesswoman, co-authored it and helped make it publishable. It became the best-selling personal finance book in history.

Scott Galloway

Scott Galloway is a serial entrepreneur and NYU Stern School of Business professor who became famous for his brutally honest takes on Big Tech. He founded nine companies over his career, including L2 (a business intelligence firm sold to Gartner in 2017), Red Envelope (an e-commerce company that went public then bankrupt), and Prophet (a brand strategy firm).

His 2017 book The Four, about Amazon, Apple, Facebook, and Google, became a bestseller. His YouTube channel and Prof G podcast reach millions.

He called Amazon buying Whole Foods before it happened. He also co-hosts Pivot with Kara Swisher, one of the most popular tech podcasts in the world.

He teaches brand strategy at NYU and is known for his profanity-laced, data-heavy lectures that go viral every semester.

Robert Kiyosaki

Rich Dad Company is his primary business — a financial education empire that includes books, seminars, board games (Cashflow, his property investing simulation game), and online courses. The brand has generated hundreds of millions in revenue.

He also runs the Rich Dad radio show and podcast.

He has made multiple real estate investments over the decades, primarily in apartment complexes and commercial properties. Rich Global LLC, one of his companies, filed for Chapter 7 bankruptcy in 2012 after losing a lawsuit to a former business partner.

He has been involved in various business disputes over the years, including settlements with former associates.

Scott Galloway

L2 Inc (founder, sold to Gartner), Red Envelope (founder, IPO then bankruptcy), Prophet (co-founder), Section4 (founder, online education), Prof G Media (founder)

Robert Kiyosaki

US Merchant Marine Academy, BS, 1969. He served in the US Marine Corps as a helicopter pilot during the Vietnam War.

He has credited military service with teaching him leadership and risk tolerance more than any academic training.

Scott Galloway

UCLA (BA), UC Berkeley Haas School of Business (MBA).